2-Methylacetophenone → (R)-1-(2-Methylphenyl)ethyl alcohol

HRID 557634Notes

Reaction equation

HRID 557634 reaction equation
B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@H]2N1CCC2.CSC.B.[CH3:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33](=[O:35])[CH3:34]>C1COCC1>[C:27]1([CH3:26])[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C@H:33]([OH:35])[CH3:34]

Participants

5

Reactant 3

HCID 113402-MethylacetophenoneHCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 7015154(R)-1-(2-Methylphenyl)ethyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

(S)-(−)-2-Methyl-CBS-oxazaborolidine (3.72 g, 13.4 mmol) was dissolved in THF (60 mL). Borane methyl sulfide complex (2M in THF; 36.6 mL, 73.3 mmol) was added, and the mixture was cooled to 0° C. 2′-Methylacetophenone (15 g, 111 mmol) in THF (30 mL) was added over 1 hour, and the mixture was then worked-up to yield a liquid with a white precipitate. Hexanes was added, the suspension was filtered to remove the precipitate, and the resulting filtrate was concentrated to give the title compound in 93% e.e.

Workup

  1. customworked-up to yield a liquid with a white precipitate
  2. filtrationthe suspension was filtered
  3. customto remove the precipitate
  4. concentrationthe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-5a7f36871f5a4ea3bc07cdf45366e51b
Source dataset
uspto-grants-2011_11
Patent number
US08058300B2

Reaction notes

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