Tetrahydrofuran → (S)-tert-Butyl 1-phenylbut-3-en-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

Triphenyl methylphosphonium bromide (13.1 g, 0.037 mol) was suspended in toluene (150 mL) and was treated with 1M potassium tert-butoxide in THF (28.8 mL, 0.8 equivalents) at 25° C. for 16 hrs. This solution was added dropwise to a suspension of Example 4C in toluene (100 mL) at −78° C. over 15 min. After 1.5 h, the mixture was warmed to 25° C. and partitioned between saturated ammonium chloride (100 mL) and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and the solvents were evaporated. The oil was redissolved in ether:hexanes (10 mL, 1:1) and filtered to remove triphenylphosphine oxide. The filtrate was evaporated and the crude residue was purified using ethyl acetate:hexanes (1:6) to give 2.4 g (49%) of the title compound.

Provenance & Evidence