3-Hydroxy-3-methyl-2-butanone → HCID 22350069, compound

Participants

Role	Name	HCID	Charge
Reactant	3-Hydroxy-3-methyl-2-butanone	HCID 8261	—
Reactant	4-Bromothioanisole	HCID 66037	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Water	HCID 962	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 22350069	HCID 22350069	—

Reaction Conditions

Temperature	75 °C

Reaction Steps

To a solution of sodium tert-butoxide (12 g, 125 mmol), XANTPHOS (2.05 g, 3.5 mmol) and Pd2(dba)3 (1.35 g, 1.5 mmol) in THF (600 mL) was added 4-bromothioanisole (20 g, 98 mmol) and 3-hydroxy-3-methyl-butan-2-one (12 g, 117 mmol). The resulting reaction mixture was heated to 75° C. for 2 h then cooled to r.t. and diluted with water. The organic extracts were washed (H2O), (brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 85:15-80:20) provided the title compound as a pale brown solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06919353B2
Source dataset	uspto-grants-2005_07
ORD ID	ord-22021106c0374a1197fbf8e5a6ebf7c2
Source note	uspto-grants-2005_07