Cesium carbonate → (S)-3-[4-[4'-(Trifluoromethyl)-3-biphenylylmethoxy]phenyl]-4-hexynoic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	3-(4-Trifluoromethylphenyl)-benzyl chloride	HCID 22280138	—
Reactant	(3S)-3-(4-Hydroxy-phenyl)-hex-4-ynoic acid methyl ester	HCID 59855119	—
Solvent	Acetone	HCID 180	—
Product	(S)-3-[4-[4'-(Trifluoromethyl)-3-biphenylylmethoxy]phenyl]-4-hexynoic acid methyl ester	HCID 59855127	—

Reaction Conditions

Temperature	50 °C

Reaction Steps

Benzyl chloride 2.3 (28.0 g, 103 mmol) and phenol 1 (21.5 g, 98 mmol) were dissolved in acetone (150 mL) and treated with Cs2CO3 (39.9 g, 122 mmol). The reaction was stirred at 50° C. for 16 hours, filtered, and concentrated to a pale yellow oil which was chromatographed (silica gel, 33% to 66% DCM in hexanes). Eluant containing compound 2.4 was concentrated to a colorless oil (40.0 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07465804B2
Source dataset	uspto-grants-2008_12
ORD ID	ord-7fbd0623a2b940b28836895d82d2cfb5
Source note	uspto-grants-2008_12