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

Participants

Role	Name	HCID	Charge
Reactant	2-Methylacetophenone	HCID 11340	—
Reactant	(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaborole	HCID 2734713	—
Reactant	(Dimethyl sulfide)trihydroboron	HCID 12423031	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(R)-1-(2-Methylphenyl)ethyl alcohol	HCID 7015154	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

(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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08058300B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-5a7f36871f5a4ea3bc07cdf45366e51b
Source note	uspto-grants-2011_11