2,2-Dimethylbutyryl chloride → HCID 14403853, compound

Participants

Reaction Steps

2,2-Dimethylbutyryl chloride (1.2 mL, 8.66 mmol) and 4-dimethylaminopyridine (1.17 g, 9.58 mmol) were added under a nitrogen atmosphere at room temperature to a solution of the alcohol prepared in the preceding paragraph (880 mg, 2.18 mmol) in 50 mL of methylene chloride. After the addition, the solution was stirred at room temperature for 5 hours. The solution was washed with 10% HCl, 10% NaHCO3, dried (anh. K2CO3) and the solvent removed under reduced pressure. Purification of the residual oil on silica gel (230-400 mesh) using 4:1 methylene chloride:hexane as an eluent gave 2,2-dimethylbutanoic acid (E)-1-[2-[2-(5,5-dimethyl-1,3-dioxan-2-yl)-ethenyl]-3,5-dimethylphenyl]decyl ester as an oil (960 mg, 88%): IR (film) 2910, 2840 and 1720 cm-1 ; NMR (DMSO-d6) δ 0.66-0.78 (6H, m), 0.86 (3H, t, J=9 Hz), 1.02-1.20 (9H, m), 1.20-1.40 (14H, m), 1.50-1.70 (2H, m), 2.20 (3H, s), 2.24 (3H, s), 3.56 (2H, d, J=10 Hz), 3.64 (2H, d, J=10 Hz), 5.10 (1H, d, J=4 Hz), 5.68 (1H, dd, J=4, 15 Hz), 5.74-5.84 (1H, m), 6.78 (1H, d, J=15 Hz), 6.98 (2H, s).

Provenance & Evidence