Sodium borohydride → HCID 86653929, compound

HRID 71080Notes

Reaction equation

HRID 71080 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:49]3[C:16](=[CH:17][C:18]4[C:19](=[O:119])[C:20]5[C:45]([C:46](=[O:50])[C:47]=4[CH:48]=3)=[CH:44][C:43]3[C:22](=[C:23]([S:108][C:109]4[CH:114]=[CH:113][C:112]([C:115]([CH3:118])([CH3:117])[CH3:116])=[CH:111][CH:110]=4)[C:24]4[C:41]([C:42]=3[S:51][C:52]3[CH:57]=[CH:56][C:55]([C:58]([CH3:61])([CH3:60])[CH3:59])=[CH:54][CH:53]=3)=[CH:40][C:39]3[C:38](=[O:62])[C:37]6[C:28](=[CH:29][C:30]7[C:35]([CH:36]=6)=[C:34]([S:63][C:64]6[CH:69]=[CH:68][C:67]([C:70]([CH3:73])([CH3:72])[CH3:71])=[CH:66][CH:65]=6)[C:33]([S:74][C:75]6[CH:80]=[CH:79][C:78]([C:81]([CH3:84])([CH3:83])[CH3:82])=[CH:77][CH:76]=6)=[C:32]([S:85][C:86]6[CH:91]=[CH:90][C:89]([C:92]([CH3:95])([CH3:94])[CH3:93])=[CH:88][CH:87]=6)[C:31]=7[S:96][C:97]6[CH:102]=[CH:101][C:100]([C:103]([CH3:106])([CH3:105])[CH3:104])=[CH:99][CH:98]=6)[C:27](=[O:107])[C:26]=3[CH:25]=4)[CH:21]=5)[C:15]([S:120][C:121]3[CH:126]=[CH:125][C:124]([C:127]([CH3:130])([CH3:129])[CH3:128])=[CH:123][CH:122]=3)=[C:14]([S:131][C:132]3[CH:137]=[CH:136][C:135]([C:138]([CH3:141])([CH3:140])[CH3:139])=[CH:134][CH:133]=3)[C:13]=2[S:142][C:143]2[CH:148]=[CH:147][C:146]([C:149]([CH3:152])([CH3:151])[CH3:150])=[CH:145][CH:144]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C1COCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11][C:12]2[C:49]3[C:16](=[CH:17][C:18]4[CH:19]([OH:119])[C:20]5[C:45]([CH:46]([OH:50])[C:47]=4[CH:48]=3)=[CH:44][C:43]3[C:22](=[C:23]([S:108][C:109]4[CH:110]=[CH:111][C:112]([C:115]([CH3:116])([CH3:117])[CH3:118])=[CH:113][CH:114]=4)[C:24]4[C:41]([C:42]=3[S:51][C:52]3[CH:53]=[CH:54][C:55]([C:58]([CH3:59])([CH3:60])[CH3:61])=[CH:56][CH:57]=3)=[CH:40][C:39]3[CH:38]([OH:62])[C:37]6[C:28](=[CH:29][C:30]7[C:35]([CH:36]=6)=[C:34]([S:63][C:64]6[CH:65]=[CH:66][C:67]([C:70]([CH3:71])([CH3:72])[CH3:73])=[CH:68][CH:69]=6)[C:33]([S:74][C:75]6[CH:80]=[CH:79][C:78]([C:81]([CH3:82])([CH3:83])[CH3:84])=[CH:77][CH:76]=6)=[C:32]([S:85][C:86]6[CH:91]=[CH:90][C:89]([C:92]([CH3:95])([CH3:94])[CH3:93])=[CH:88][CH:87]=6)[C:31]=7[S:96][C:97]6[CH:102]=[CH:101][C:100]([C:103]([CH3:106])([CH3:105])[CH3:104])=[CH:99][CH:98]=6)[CH:27]([OH:107])[C:26]=3[CH:25]=4)[CH:21]=5)[C:15]([S:120][C:121]3[CH:122]=[CH:123][C:124]([C:127]([CH3:130])([CH3:129])[CH3:128])=[CH:125][CH:126]=3)=[C:14]([S:131][C:132]3[CH:137]=[CH:136][C:135]([C:138]([CH3:141])([CH3:140])[CH3:139])=[CH:134][CH:133]=3)[C:13]=2[S:142][C:143]2[CH:148]=[CH:147][C:146]([C:149]([CH3:152])([CH3:151])[CH3:150])=[CH:145][CH:144]=2)=[CH:9][CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86653930HCID 86653930, compound

Product 1

HCID 86653929HCID 86653929, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1,2,3,4,8,12,13,14,15,19-deca(4′-t-butylphenylthio)nonacene-6,10,17,21-tetraone (0.5 g, 0.23 mmol) in dry THF (10 mL) under a N2 atmosphere was slowly added NaBH4 (0.1 g, 2.64 mmol). The reaction mixture was stirred at room temp for 3 h, and then quenched with H2O. The resulting mixture was filtered, washed with H2O, and dried in vacuo to give the desired product as a light yellow solid (0.47 g, 94%). LDI-MS m/z: 2188 [M+], 2171 [M+-OH]. The laser desorption ionization mass spectrum (LDI-MS) of 1,2,3,4,8,12,13,14,15,19-deca(4′-t-butylphenylthio)-6,10,17,21-tetrahydrononacene-6,10,17,21-tetraol is shown in FIG. 14B. The compound structure is shown in FIG. 14A.

Workup

  1. customquenched with H2O
  2. filtrationThe resulting mixture was filtered
  3. washwashed with H2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-a41c3323989c49938ebaa75d2608b6e6
Source dataset
uspto-grants-2014_09
Patent number
US08822731B2

Reaction notes

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