Triethoxysilane → 4-Phenyl-2-butanol

HRID 1588023Notes

Reaction equation

HRID 1588023 reaction equation
C(O[SiH](OCC)OCC)C.[C:11]1([CH2:17][CH2:18][C:19](=[O:21])[CH3:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>CC(C)[O-].[Dy+3].CC(C)[O-].CC(C)[O-].C1COCC1>[C:11]1([CH2:17][CH2:18][CH:19]([OH:21])[CH3:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 13830TriethoxysilaneHCID 14798Sodium HydroxideHCID 17355Benzyl acetone

Product 1

HCID 613024-Phenyl-2-butanolYield 52%

Reagents, catalysts & solvents 2

HCID 13033546Dysprosium tripropan-2-olateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A dry Schlenk tube under argon was charged with 51 mg (0.15 mmol) of dysprosium (III) isopropoxide. Triethoxysilane (1.4 mL, 7.5 mmol) was added, and the reaction mixture was heated to 60° C. After 0.5 hours, 4-phenyl-2-butanone (450 μL, 3 mmol) was added. After 24 hours, the reaction was complete, as determined by GLC analysis of a aliquot taken from the reaction mixture. THF (8 mL) and aqueous NaOH (1 N, 15 mL) were added, and the mixture was stirred vigorously for 12 hours. After work-up as in Example 13, the crude material was purified by flash chromatography (ether:hexane=3:7) to afford 234 mg (52% yield) of 4-phenyl-2-butanol (>95% pure by 1H-NMR analysis).

Workup

  1. waitAfter 24 hours
  2. customAfter work-up as in Example 13, the crude material was purified by flash chromatography (ether:hexane=3:7)

Sources & evidence

ORD record
ord-63e4f63e66e54ed8bdc2bf16ca59989b
Source dataset
uspto-grants-1993_06
Patent number
US05220020

Reaction notes

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