Sulfoxonium, trimethyl-, iodide (1:1) → (3-(Benzyloxy)phenyl)(2-methylcyclopropyl)methanone

Participants

Role	Name	HCID	Charge
Reactant	Sulfoxonium, trimethyl-, iodide (1:1)	HCID 74498	—
Reactant	1,8-Diazabicyclo(5.4.0)undec-7-ene	HCID 81184	—
Reactant	(E)-1-(3-(Benzyloxy)phenyl)but-2-en-1-one	HCID 57706211	—
Solvent	Acetonitrile	HCID 6342	—
Product	(3-(Benzyloxy)phenyl)(2-methylcyclopropyl)methanone	HCID 57706540	36.3%

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a solution of 93.C (5.33 g, 21.1 mmol) in ACN (200 mL) were added trimethylsulfoxonium iodide (available from Aldrich) (5.58 g, 25.3 mmol) and DBU (4.11 mL, 27.5 mmol). The mixture was stirred overnight at 60° C. under N2, cooled to room temperature, and concentrated. The crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford 93.D (2.04 g, 36% yield) as a colorless oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08030354B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-73e4047b6c164f9caaee95197e9161f1
Source note	uspto-grants-2011_10