Citric Acid → HCID 59127832, compound

Participants

Reaction Steps

A solution of 1.01 g (3.69 mmol) of the resultant compound of Example 29 in 50 ml of anhydrous tetrahydrofuran was cooled under N2 atmosphere to -78° C. and treated with 16 ml (9.6 mmol) of vinylmagnesium bromide (0.6M in tetrahydrofuran). The resulting solution was allowed to warm to ambient temperature, stirred for 1.5 h, and poured over a mixture of ice and 10% aqueous citric acid. The mixture was extracted with ether, washed with saturated brine, dried over MgSO4, and concentrated in vacuo. Silica gel chromatography of the residue using 12% ethyl acetate in hexane provided 0.48 g (58%) of the desired compound (Rf 0.48, 7:3 hexane:ethyl acetate). 1H NMR (CDCl3) δ 0.93 (d, J=7 Hz, 3 H), 1.00 (d, J=7 Hz, 1 H), 1.3-1.45 (m, 2 H), 1.43 (s, 9 H), 1.74 (m, 1 H), 4.65 (td, J=9, 4 H, 1 H), 5.09 (br d, 1 H), 5.88 (dd, J=10, 2 Hz, 1 H), 6.38 (dd, J=18, 2 Hz, 1 H), 6.48 (dd, J=18, 10 Hz, 1 H). Mass spectrum: (M+H)+ =242.

Provenance & Evidence