Ethyl Acetate → 1-Propanol, 3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-methyl-, (R)-

HRID 1609785Notes

Reaction equation

HRID 1609785 reaction equation
[Si:1]([O:18][CH2:19][C@H:20]([CH3:25])[C:21](OC)=[O:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.CCCCCC.C(OCC)(=O)C.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[Si:1]([O:18][CH2:19][C@H:20]([CH3:25])[CH2:21][OH:22])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 11302759(2S)-3-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-2-methylpropanoic Acid Methyl EsterHCID 131725251DIBAL n-hexane

Product 1

HCID 117718171-Propanol, 3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-methyl-, (R)-Yield 109.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under argon atmosphere, Methyl(S)-3-(t-butyldiphenylsilyloxy)-2-metylpropionate (47) (1.0 g, 2.7 mmol) was dissolved in 50 ml of dry toluene, 1M DIBAL-H/hexane (5.7 ml, 5.7 mmol) was added to the resultant solution at 0° C., and the mixture was stirred for 15 min. Subsequently, the reaction mixture was further stirred for 45 min after the temperature was returned to room temperature. Ethyl acetate was added to the reaction mixture to decompose the excess DIBAL-H, and the resultant mixture was extracted with 0.5N HCl. The ethyl acetate layer was washed with brine, dried over magnesium sulfate and evaporated. The obtained crude product was purified by column chromatography (30 g, 4-10% AcOEt-hexane) to obtain a colorless oily product (48) (968 mg, quant.).

Workup

  1. stirringSubsequently, the reaction mixture was further stirred for 45 min after the temperature
  2. customwas returned to room temperature
  3. extractionthe resultant mixture was extracted with 0.5N HCl
  4. washThe ethyl acetate layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe obtained crude product
  8. customwas purified by column chromatography (30 g, 4-10% AcOEt-hexane)

Sources & evidence

ORD record
ord-dba47961fa304c988b59d85a5332202a
Source dataset
uspto-grants-2006_01
Patent number
US06982257B1

Reaction notes

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