Diethyl Ether → HCID 86659447, compound

Participants

Reaction Conditions

Reaction Steps

In a flask, isobutyronitrile (6.39 g, 92.4 mmol) was dissolved in diethyl ether (190 mL) and cooled at −78° C. NaHMDS (1.0 M in THF, 99.0 mL, 99.0 mmol) was added and the mixture stirred for 30 min at −78° C. A solution of (R)-2-methyl-propane-2-sulfinic acid (E)-ethylideneamide (crude from step 1, 5.21 g, 33.0 mmol) in THF (50.0 mL) was slowly added. The mixture was stirred at −78° C. for 2 h then allowed to warm to room temperature overnight. The reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4 and concentrated. The residue was purified by SiO2 chromatography (20-100% EtOAc/hexane) to afford 2.93 g (41%) (R)-2-methyl-propane-2-sulfinic acid ((S)-2-cyano-1,2,2-trimethyl-ethyl)-amide as a light yellow oil. 1H NMR (CDCl3, 300 MHz): δ (ppm) 3.28 (dq, J=8.7, 6.4 Hz, 1H), 3.08 (d, J=8.7 Hz, 1H), 1.45 (d, J=6.4 Hz, 3H), 1.39 (s, 3H), 1.34 (s, 3H), 1.26 (s, 9H).

Provenance & Evidence