Pivalaldehyde → HCID 69466803, compound

Participants

Reaction Steps

Prepared according to the method of paragraph C by reaction of N-propionyl-2-benzoxazolone with trimethylacetaldehyde. Slow addition of the aldehyde to the enolate solution over 1 hour at 0° C. gave a 9:1 ratio of the (2R*,3S*) and (2R*,3R*) isomers. The desired isomer was crystallized from 1:1 ether/hexanes, mp=90-2° C. 1H-NMR (CDCl3, 400 MHz) δ 8.04 (m, 1H), 7.23-7.29 (m, 3H), 4.32 (dq, J=3, 7 Hz, 1H), 3.79 (d, J=10 Hz, 1H), 3.41 (dd, J=3,10 Hz, 1H), 1.51 (d, J=7 Hz, 3H), 0.94 (s, 9H). 13C-NMR (CDCl3, 100 MHz) δ 178.2, 150.8, 142.0, 127.6, 125.7, 125.0, 116.3, 110.0, 84.0, 37.4, 36.2, 26.7, 18.1.

Provenance & Evidence