Acetophenone → 1-Phenylethanol, (R)-

HRID 2092456Notes

Reaction equation

HRID 2092456 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@H]2N1CCC2.CSC.B>C1COCC1>[C:4]1([C@H:1]([OH:3])[CH3:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7410AcetophenoneHCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 6375161-Phenylethanol, (R)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To acetophenone (19.47 mL, 166.6 mmol) in THF (100 mL) was added (S)-(−)-2-methyl-CBS-oxazaborolidine (4.62 g, 16.6 mmol), and the reaction was cooled to 0° C. Borane methyl sulfide complex (2M in THF; 50 mL, 100 mmol) was added over 15 minutes, and the reaction was stirred at room temperature. Aqueous work-up gave the title compound.

Sources & evidence

ORD record
ord-d20e401119114df09f510a7bfa7078c4
Source dataset
uspto-grants-2013_05
Patent number
US08440707B2

Reaction notes

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