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Sodium borohydride → HCID 86588696, compound

HRID 6582
Notes
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Reaction equation

HRID 6582 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:178]=[C:179]([C:181]([CH3:184])([CH3:183])[CH3:182])[CH:180]=1)[CH:8]=[CH:9][C:10]1[CH:11]=[C:12]([CH:159]=[C:160]([CH:162]=[CH:163][C:164]2[CH:169]=[C:168]([C:170]([CH3:173])([CH3:172])[CH3:171])[CH:167]=[C:166]([C:174]([CH3:177])([CH3:176])[CH3:175])[CH:165]=2)[CH:161]=1)[CH:13]=[CH:14][C:15]1[CH:16]=[C:17]([CH:116]=[C:117]([CH:119]=[CH:120][C:121]2[CH:126]=[C:125]([CH:127]=[CH:128][C:129]3[CH:134]=[C:133]([C:135]([CH3:138])([CH3:137])[CH3:136])[CH:132]=[C:131]([C:139]([CH3:142])([CH3:141])[CH3:140])[CH:130]=3)[CH:124]=[C:123]([CH:143]=[CH:144][C:145]3[CH:150]=[C:149]([C:151]([CH3:154])([CH3:153])[CH3:152])[CH:148]=[C:147]([C:155]([CH3:158])([CH3:157])[CH3:156])[CH:146]=3)[CH:122]=2)[CH:118]=1)[CH:18]=[CH:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([CH:28]=[CH:29][C:30]2[CH:35]=[C:34]([CH:36]=[CH:37][C:38]3[CH:43]=[C:42]([CH:44]=[CH:45][C:46]4[CH:51]=[C:50]([C:52]([CH3:55])([CH3:54])[CH3:53])[CH:49]=[C:48]([C:56]([CH3:59])([CH3:58])[CH3:57])[CH:47]=4)[CH:41]=[C:40]([CH:60]=[CH:61][C:62]4[CH:67]=[C:66]([C:68]([CH3:71])([CH3:70])[CH3:69])[CH:65]=[C:64]([C:72]([CH3:75])([CH3:74])[CH3:73])[CH:63]=4)[CH:39]=3)[CH:33]=[C:32]([CH:76]=[CH:77][C:78]3[CH:83]=[C:82]([CH:84]=[CH:85][C:86]4[CH:91]=[C:90]([C:92]([CH3:95])([CH3:94])[CH3:93])[CH:89]=[C:88]([C:96]([CH3:99])([CH3:98])[CH3:97])[CH:87]=4)[CH:81]=[C:80]([CH:100]=[CH:101][C:102]4[CH:107]=[C:106]([C:108]([CH3:111])([CH3:110])[CH3:109])[CH:105]=[C:104]([C:112]([CH3:115])([CH3:114])[CH3:113])[CH:103]=4)[CH:79]=3)[CH:31]=2)[CH:27]=1)[CH:23]=[O:24])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>O1CCCC1>[C:56]([C:48]1[CH:47]=[C:46]([CH:51]=[C:50]([C:52]([CH3:55])([CH3:54])[CH3:53])[CH:49]=1)[CH:45]=[CH:44][C:42]1[CH:43]=[C:38]([CH:39]=[C:40]([CH:60]=[CH:61][C:62]2[CH:67]=[C:66]([C:68]([CH3:71])([CH3:70])[CH3:69])[CH:65]=[C:64]([C:72]([CH3:75])([CH3:74])[CH3:73])[CH:63]=2)[CH:41]=1)[CH:37]=[CH:36][C:34]1[CH:35]=[C:30]([CH:31]=[C:32]([CH:76]=[CH:77][C:78]2[CH:79]=[C:80]([CH:100]=[CH:101][C:102]3[CH:103]=[C:104]([C:112]([CH3:114])([CH3:113])[CH3:115])[CH:105]=[C:106]([C:108]([CH3:111])([CH3:110])[CH3:109])[CH:107]=3)[CH:81]=[C:82]([CH:84]=[CH:85][C:86]3[CH:91]=[C:90]([C:92]([CH3:95])([CH3:94])[CH3:93])[CH:89]=[C:88]([C:96]([CH3:99])([CH3:98])[CH3:97])[CH:87]=3)[CH:83]=2)[CH:33]=1)[CH:29]=[CH:28][C:26]1[CH:25]=[C:22]([CH:21]=[C:20]([CH:19]=[CH:18][C:17]2[CH:16]=[C:15]([CH:14]=[CH:13][C:12]3[CH:11]=[C:10]([CH:9]=[CH:8][C:7]4[CH:178]=[C:179]([C:181]([CH3:183])([CH3:182])[CH3:184])[CH:180]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=4)[CH:161]=[C:160]([CH:162]=[CH:163][C:164]4[CH:169]=[C:168]([C:170]([CH3:173])([CH3:172])[CH3:171])[CH:167]=[C:166]([C:174]([CH3:177])([CH3:176])[CH3:175])[CH:165]=4)[CH:159]=3)[CH:118]=[C:117]([CH:119]=[CH:120][C:121]3[CH:126]=[C:125]([CH:127]=[CH:128][C:129]4[CH:134]=[C:133]([C:135]([CH3:136])([CH3:137])[CH3:138])[CH:132]=[C:131]([C:139]([CH3:140])([CH3:141])[CH3:142])[CH:130]=4)[CH:124]=[C:123]([CH:143]=[CH:144][C:145]4[CH:146]=[C:147]([C:155]([CH3:156])([CH3:157])[CH3:158])[CH:148]=[C:149]([C:151]([CH3:152])([CH3:153])[CH3:154])[CH:150]=4)[CH:122]=3)[CH:116]=2)[CH:27]=1)[CH2:23][OH:24])([CH3:57])([CH3:58])[CH3:59]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 542800983,5-Bis{3',5'-bis[3'',5''-bis(3''',5'''-di-tert-butylstyryl)styryl]styryl}benzaldehyde

Product 1

HCID 86588696HCID 86588696, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of 3,5-bis{3′,5′-bis[3″,5″-bis(3′″,5′″-di-tert-butylstyryl)styryl]styryl}benzaldehyde (3.853 g, 1.585 mmol) in tetrahydrofuran (50 cm3) was treated with sodium borohydride (121 mg, 3.20 mmol) and heated at reflux for 135 min. The solvent was removed. Dichloromethane (50 cm3) was added and the solution washed with water (50 cm3) and brine (50 cm3), dried over sodium sulphate, filtered and the solvent removed to leave a yellow foam. The product was purified by column chromatography over silica, eluting with dichloromethane-light petroleum (2:3). Recrystallisation from a dichloromethane-methanol mixture gave 3,5-bis{3′,5′-bis[3″,5″-bis(3′″,5′″-di-tert-butylstyryl)styryl]styryl}benzyl alcohol (3.07 g, 80%) as a yellow powder, mp 248° C. (Found: C, 89.89; H, 8.89. C183H220O requires C, 90.24; H, 9.10%); vmax(KBr)/cm−1 3568 (OH), 1594 (C═C) and 959 (C═C—H trans); λmax(CH2Cl2)/nm (log ε) 323 (5.59) and 334sh (5.52); δH(400 MHz, CDCl3) 1.39 (144H, s, t-Bu), 1.80 (1H, t, OH), 4.85 (2H, d, CH2OH), 7.19 and 7.31 (16H, ABq, J 16, 7′″, 8′″-H), 7.32(4H, s, 7′, 8′-H), 7.34(8H, s, 7″, 8″-H), 7.38 (8H, dd, J 1.5, 4′″-H), 7.44 (16H, d, J 1.5, 2′″, 6′″-H), 7.57(2H, br s, 4′-H), 7.67 (12H, br s, 2″, 4″, 6″-H), 7.67 (4H, br s, 2′, 6′-H), 7.70 (1H, br s, 4-H) and 7.74 (2H, br s, 2, 6-H); m/z (MALDI) 2434.94 (M+, 100%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 135 min
  3. customThe solvent was removed
  4. additionDichloromethane (50 cm3) was added
  5. washthe solution washed with water (50 cm3) and brine (50 cm3)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customthe solvent removed
  9. customto leave a yellow foam
  10. customThe product was purified by column chromatography over silica
  11. washeluting with dichloromethane-light petroleum (2:3)
  12. customRecrystallisation from a dichloromethane-methanol mixture

Sources & evidence

ORD record
ord-042ea76dc6784c55b2a71fe62bfbe739
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07083862B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes