Pivalaldehyde → HCID 69465281, compound

Participants

Reaction Steps

Prepared according to the method of paragraph C by reaction of N-propionyl-2-benzoxazolone with trimethylacetaldehyde. Rapid addition of the aldehyde to the enolate solution at 0° C. gave a 1:1 ratio of the (2R*,3S*) and (2R*,3R*) isomers. The desired isomer was isolated by silica gel chromatography, then crystallized. 1-NMR (CDCl3, 400 MHz): δ 8.05 (m, 1 H), 7.20–7.27 (m, 4 H), 4.24 (dq, J=7, 4 Hz, 1 H), 3.82 (br t, J=4 Hz, 1 H), 2.33 (br d, J=4 Hz, 1 H), 1.36 (d, J=7 Hz, 3 H), 0.99, (s, 9 H). 13C-NMR (CDCl3, 100 MHz): δ 175.3, 150.8, 142.2, 127.9, 125.4, 124.9, 116.2, 109.9, 77.6, 40.3, 35.8, 29.7, 26.7, 12.7.

Provenance & Evidence