Sodium borohydride → HCID 131711718, compound

HRID 127559Notes

Reaction equation

HRID 127559 reaction equation
[O:1]([CH2:19][CH:20]([CH3:51])[CH2:21][CH2:22][CH2:23][C:24]([CH3:50])([O:46][CH2:47][S:48][CH3:49])[C:25](=[O:45])[CH2:26][CH2:27][C:28]1([O:44][CH2:43][CH2:42][O:41]1)[CH2:29][O:30][S:31]([C:34]1[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=1)(=[O:33])=[O:32])[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[O:1]([CH2:19][CH:20]([CH3:51])[CH2:21][CH2:22][CH2:23][C:24]([CH3:50])([O:46][CH2:47][S:48][CH3:49])[CH:25]([OH:45])[CH2:26][CH2:27][C:28]1([O:44][CH2:43][CH2:42][O:41]1)[CH2:29][O:30][S:31]([C:34]1[CH:35]=[CH:36][C:37]([CH3:38])=[CH:39][CH:40]=1)(=[O:32])=[O:33])[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131711716HCID 131711716, compound

Product 1

HCID 131711718HCID 131711718, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

11-t-Butyldiphenylsiloxy-6,10-dimethyl-2,2-ethylenedioxy-6-methylthiomethoxy-5-oxo-1-tosyloxyundecane (0.493 g) in methanol (30 ml) is cooled to 0° C.; sodium borohydride (0.438 g) is added and the resulting solution is stirred for 2 hours. The solvent is removed in vacuo and the residue is neutralized to pH 7 with aqueous hydrochloric acid and extracted with ether. The ether extract is washed with brine and dried over sodium sulfate. The solvent is removed in vacuo to give 11-t-butyldiphenylsiloxy-6,10-dimethyl-2,2-ethylenedioxy-5-hydroxy-6-methylthiomethoxy-1-tosyloxyundecane (0.481 g) as an epimeric mixture of alcohols. The alcohols are separated by chromatography on silica employing ethyl acetate:hexane as the eluting solvent. The epimers have the following nmr spectra:

Workup

  1. customThe solvent is removed in vacuo
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-6451b7b295c84c13a8b9d28382bedaf1
Source dataset
uspto-grants-1981_03
Patent number
US04256644

Reaction notes

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