Diethyl Ether → Ethyl 3-methyltridec-2E-enoate

Participants

Reaction Conditions

Reaction Steps

Decyl magnesium bromide (2.4 mL of a 2.0 M soln in ether, 4.8 mmol) CuCN (221 mg, 2.49 mmol) were suspended in anhydrous ether and cooled to −78° C. The mixture was warmed to 0° C. for 5 minutes and cooled to −78° C. The triflate D (220 mg, 0.83 mmol) was dissolved in anhydrous ether and added to the decyl magnesium and CuCN solution dropwise. The mixture was stirred vigorously for 2.5 hours. The solution was then warmed to 0° C. and quenched with a 10% aqueous ammonium chloride solution. The layers were separated, and the aqueous layer was extracted with ethyl acetate (3×10 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated. Purification by flash chromatography (19:1 hexane/ethyl acetate) gave E in a yield of 75% (150 mg). 1H NMR (300 MHz, CDCl3): δ 0.8 (t, 3H), 1.25 (narrow m, 20H), 1.4 (s, 3H), 1.6 (2H), 3.6 (t, 3H), 4.2 (q, 2H) and 5.9 (s, 1H).

Provenance & Evidence