2-Methoxypropene → HCID 10592560, compound

Participants

Reaction Steps

Pyridinium p-toluenesulfonate (90 mg) was added to a solution of methyl (S)-3-hydroxytetradecanoate (VIII, 10.32 g, 40 mmol) in 2-methoxypropen (40 mL). After stirring for 20 min at room temperature the reaction mixture was diluted with diethyl ether (30 mL) and extracted first with a saturated aqueous solution of sodium hydrogen carbonate (3 mL) and then with water (2×2 mL). The combined organic phases were dried (Na2SO4) and concentrated under reduced pressure. The residual colorless oil (13.20 g, 99%) was used in the next step without further purification. [α]25D +10.01 (c=0.5 in hexane); 1H NMR (DMSO-D6) δ 0.86 (t, J=7 Hz, 3H), 1.24-1.27 (m, 26H), 1.44-1.46 (m, 2H), 3.09 (s, 3H), 3.58 (s, 3H), 4.03-4.05 (m, 1H); 13C NMR (DMSO-D6) δ 13.85, 22.02, 22.05, 24.26, 24.86, 28.67, 28.91, 28.97, 28.98, 29.03, 30.93, 31.27, 35.13, 40.21, 48.46, 51.15, 67.67, 100.35, 171.62. Anal. Calcd for C19H38O4 : C, 69.05; H, 11.59. Found: C, 69.00; H, 11.63.

Provenance & Evidence