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Sodium borohydride → HCID 86588696, 화합물

HRID 2245191
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HRID 2245191 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

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

생성물 1

HCID 86588696HCID 86588696, 화합물수율 80%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

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%); νmax(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 (144 H, s, t-Bu), 1.80 (1 H, t, OH), 4.85 (2 H, d, CH2OH), 7.19 and 7.31 (16 H, ABq, J 16, 7′″,8′″-H), 7.32 (4 H, s, 7′,8′-H), 7.34 (8 H, s, 7″,8″-H), 7.38 (8 H, dd, J 1.5, 4′″-H), 7.44 (16 H, d, J 1.5, 2′″,6′″-H), 7.57 (2 H, br s, 4′-H), 7.67 (12 H, br s, 2″,4″,6″-H), 7.67 (4 H, br s, 2′,6′-H), 7.70 (1 H, br s, 4-H) and 7.74 (2 H, br s, 2,6-H); m/z (MALDI) 2434.94 (M+, 100%).

후처리

  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

출처 및 근거

ORD 기록
ord-4d7b971cfd11465aa33e30c22aabdaf1
출처 데이터셋
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07682708B2

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