Sodium borohydride → HCID 86678089, compound

HRID 2274715Notes

Reaction equation

HRID 2274715 reaction equation
[CH2:1]([CH:18]([CH:39]([OH:57])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]/[CH:47]=[CH:48]\[CH2:49]/[CH:50]=[CH:51]\[CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[C:19](=[O:38])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].O(O)O.[BH4-].[Na+]>CO.C(O)(C)C>[CH2:1]([CH:18]([CH:19]([OH:38])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:39]([OH:57])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]/[CH:47]=[CH:48]\[CH2:49]/[CH:50]=[CH:51]\[CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 86678090HCID 86678090, compound

Product 1

HCID 86678089HCID 86678089, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

A solution of the keto-alcohol (6Z,9Z,29Z,32Z)-20-((8Z,11Z)-heptadeca-8,11-dien-1-yl)-21-hydroxyoctatriaconta-6,9,29,32-tetraen-19-one (10) (920 mg, 1.16 mmol) in CH3OH (5 mL) and isopropanol (12 mL) was treated with NaBH4 (88 mg, 2.3 mmol). After stirring (1 h) a second portion of NaBH4 (88 mg, 23 mmol) was added and the mixture stirred (3 h). The reaction mixture was carefully quenched by the addition of cold HCl (5% aq.), extracted with CH2Cl2, washed with brine, dried (Na2SO4), filtered and concentrated. The crude material was subjected to chromatography (1%→10% EtOAc-hexanes) to yield (6Z,9Z,29Z,32Z)-19-((8Z,11Z)-heptadeca-8,11-dien-1-yl)octatriaconta-6,9,29,32-tetraene-18,20-diol (11) (832 mg, 90%) as a colorless oil. Rf 0.23 (10% EtOAc-hexanes), FW 793.39, C55H100O2.

Workup

  1. additionwas added
  2. customThe reaction mixture was carefully quenched by the addition of cold HCl (5% aq.)
  3. extractionextracted with CH2Cl2
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3723b407e4b24b0b96fa0dec4149b367
Source dataset
uspto-grants-2015_09
Patent number
US09126966B2

Reaction notes

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