Triethoxysilane → 4-Phenyl-2-butanol

HRID 1588024Notes

Reaction equation

HRID 1588024 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-].[Y+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-butanol

Reagents, catalysts & solvents 2

HCID 11550724Yttrium(iii) isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A dry Schlenk tube under argon was charged with 37 mg (0.15 mmol) of yttrium (III) isopropoxide (Y5O(iPrO)13). 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 235 mg (of 4-phenyl-2-butanol (>93% pure by 1H-NMR analysis, 48% adjusted yield).

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-64f24429b9c640baa4c85734ede27291
Source dataset
uspto-grants-1993_06
Patent number
US05220020

Reaction notes

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