Acetic Acid → HCID 66617733, compound

Participants

Reaction Steps

A solution of 28 (3.2 g; 8.1 mmol) in 60 mL of THF and acetic acid (1.16 mL; 20.3 mmol) was treated with TBAF 1M in THF. The reaction mixture was stirred for 16 h then was diluted with CH2Cl2 (120 mL) and washed with water (75 mL). The organic layer was dried with sodium sulfate and concentrated in vacuo to a yellow oil. Flash chromatography (60% EtOAc/40% hexanes) afforded 1.81 g (81%) of the desired product 29. 1H NMR (CDCl3) δ 6.2 (bs, 1H), 6.1 (bs, 1H), 3.8 (d, 1H), 3.6 (m, 2H), 3.3 (s, 1H), 3.15 (dd, 1H), 3.1 (s, 1H), 2.5 (dd, 1H), 1.5 (app.t, 3H), 1.35 (s, 9H) ppm.

Provenance & Evidence