Sodium hydride → (R,E)-Methyl 5-(3-(1,1-dioxido-3-(3-oxo-4-(3-(trifluoromethyl)phenyl)-but-1-en-1-yl)isothiazolidin-2-yl)propyl)thiophene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (12 mg, 0.5 mmol) in THF (1.0 mL) cooled to 0° C. was added a solution of dimethyl (2-oxo-3-(3-(trifluoromethyl)phenyl)propyl)-phosphonate (160 mg, 0.52 mmol) in THF (2.0 mL). After 15 min a solution of the aldehyde 11 (155 mg, 0.47 mmol) in THF (2.0 mL) was added. The reaction was allowed to warm room temperature and stirred for 16 h. The reaction was quenched with saturated aqueous ammonium chloride and extracted with EtOAc. The organic portion was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 40% EtOAc/hex) afforded 240 mg (99%) of enone 12.

Provenance & Evidence