Hydrochloric Acid → HCID 22266846, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-acetyl-8-(tert-butyldimethylsilyloxy)-2-methyloctanoate (13.5 g, 37.65 mmol) was dissolved in 10 mL CH3OH to which 5 g NaOH in 50 mL water was then added. The mixture was then heated to 50° C. overnight. The volume of the reaction mixture was reduced to about 50 mL under reduced pressure and acidified to pH 1 by the addition of 2 M HCl. This resulting mixture was heated to 60° C. for 5 hours. After cooling to room temperature the product was extracted into EtOAc. Concentration gave a yellow oil that was subjected to silica gel chromatography affording a colorless oil (4.25 g, 65.5%). 1H-NMR (300 MHz, CDCl3): δ 3.60 (t, 2H) 2.46 (m, 1H), 2.09 (s, 3H), 1.54 (m, 4H), 1.30 (m, 6H), 1.04 (d, 3H) ppm; MS m/z calculated for C10H20O2 (M+H): 173.2. Found 173.1 (M+H, ESI+).

Provenance & Evidence