Triethylamine → HCID 79179474, compound

Participants

Reaction Steps

According to a reported procedure41 with some modifications, a solution of α-methoxyacetic acid (6e, 1.17 g, 13.0 mmol) in anhydrous CH2Cl2 (20 mL) was treated portionwise with 1,1′-carbonyldiimidazole (2.54 g, 15.7 mmol) at 0° C. under argon. The ice bath was removed, and the reaction mixture was stirred for 30 min at room temperature. The reaction mixture was treated with triethylamine (2.18 mL, 15.7 mmol) and N,O-dimethylhydroxylamine hydrochloride (1.53 g, 15.6 mmol) at 0° C. The reaction mixture was stirred overnight at room temperature under argon. Saturated aqueous NH4Cl was added. The organic phase was washed with water, dried (Na2SO4) and concentrated to a transparent oil. A solution of the crude amide was treated dropwise with 2-methyl-1-propenylmagnesium bromide (28.7 mL, 14.4 mmol, 0.5 M in THF) at −20° C. under argon. The reaction mixture was stirred for 2 h under argon at 0° C. upon which a white precipitate was formed. The mixture was diluted with Et2O and treated with saturated aqueous NH4Cl. The aqueous phase was extracted with ether (3×50 mL). The combined organic extract was washed (water, brine), dried (Na2SO4), concentrated and chromatographed [silica, hexanes/EtOAc (3:1)] to afford an orange liquid (360 mg, 22%): 1H NMR δ 1.93 (s, 3H), 2.20 (s, 3H), 3.43 (s, 3H), 4.01 (s, 2H), 6.19-6.20 (m, 1H); 13C NMR δ 21.4, 28.2, 59.4, 78.5, 119.6, 158.3, 197.9; ESI-MS obsd 151.0731, calcd 151.073 [(M+Na)+, M=C7H12O2]; IR (neat) 3451, 2979, 2935, 2825, 1699, 1618, 1447, 1379, 1227, 1200, 1109, 1038, 986, 934, 815 cm−1.

Provenance & Evidence