(Diethylamino)sulfur trifluoride → HCID 86635272, compound

Participants

Reaction Conditions

Reaction Steps

4-[1-(Dimethoxy-phosphoryl)-1-hydroxy-ethyl]-benzoic acid methyl ester (0.60 g, 2.08 mmol) was added over 30 minutes to a stirring solution of DAST (1M in CH2Cl2) cooled to −78° C. under a dry nitrogen environment. The mixture was warmed to ambient temperature and stirred. After stirring for 90 minutes the reaction mixture was carefully quenched with ethanol containing pyridine (pyr: twice volume of DAST). After stirring for 30 mins the mixture was poured into ice cold water and extracted into DCM (3×). The combined organic extracts were washed with dilute HCl, water, brine, dried (MgSO4) then concentrated in vacuo. The material was carried forward without further purification. MS: cal'd 291 (MH+), exp 291 (MH+)

Provenance & Evidence