Acetic Acid → 1-[3-(tert-butyldimethylsilyloxymethyl)-phenyl]-(1E)-undecen-3-ol

HRID 977591Notes

Reaction equation

HRID 977591 reaction equation
[BH4-].[Na+].[Si:3]([O:10][CH2:11][C:12]1[CH:13]=[C:14](/[CH:18]=[CH:19]/[C:20](=[O:29])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:15]=[CH:16][CH:17]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].C(O)(=O)C>CO.O>[Si:3]([O:10][CH2:11][C:12]1[CH:13]=[C:14](/[CH:18]=[CH:19]/[CH:20]([OH:29])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:15]=[CH:16][CH:17]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 156617891-[3-(tert-butyldimethylsilyloxymethyl)-phenyl]-(1E)-undecen-3-one

Product 1

HCID 156617911-[3-(tert-butyldimethylsilyloxymethyl)-phenyl]-(1E)-undecen-3-olYield 86.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

483 mg of sodium borohydride is added to a solution of 6.5 g of the above-produced ketone in 270 ml of methanol under argon at 0° C. and stirred for one hour at this temperature. Then, it is mixed with 1.5 ml of glacial acetic acid, diluted with 150 ml of water and extracted three times with 200 ml of ethyl acetate each. The organic phase is washed neutral with brine, dried on magnesium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel. With hexane/0-20% ethyl acetate, 5.65 g of 1-[3-(tert-butyldimethylsilyloxymethyl)-phenyl]-(1E)-undecen-3-ol is obtained as colorless oil.

Workup

  1. extractionextracted three times with 200 ml of ethyl acetate each
  2. washThe organic phase is washed neutral with brine
  3. customdried on magnesium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-8d174fa90f2d4546a3a18e1b7babbcf7
Source dataset
uspto-grants-1997_03
Patent number
US05614634

Reaction notes

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