Hydrochloric Acid → 4-(3-Thienyl)-3-butenoic acid

Participants

Reaction Conditions

Reaction Steps

To a stirring suspension of 1.60 g (67 mmol) of NaH in 20 mL of THF cooled to -60° C. was added a solution of 12.36 g (33 mmol) of (2-carboxyethyl)triphenylphosphonium chloride (28), prepared in the manner described above in Example 28, and 3.75 g (33 mmol) of 3-thiophene carboxaldehyde in 40 mL of dimethylsulfoxide (DMSO)/THF (3:1). The reaction was stirred for 16 hours at -20° C., and then for 6 hours at 0° C. The reaction was then added to cold H2O. The pH was adjusted to 2 with 2 N HCl. The aqueous layer was extracted with 4×200 mL of EtOAc. The organic layer was treated as described above in Example 14 and chromatographed to yield 3.41 g (61%) of 4-(3-thienyl)-3-butenoic acid (29).

Provenance & Evidence