Diethyl Ether → HCID 11206192, compound

Participants

Reaction Steps

To a suspension of pyridinium chlorochromate (36.0 g, 167 mmol) in methylene chloride (200 mL) was added 10 (17.27 g, 92.8 mmol), whereupon the mixture became a dark homogenous solution. The reaction was stirred overnight. Diethyl ether (3×300 mL) was added and the product was passed through a short column of florisil to remove the chromium salts. Removal of the solvent in vacuo gave an oil (15.9 g, 93% yield). This was carried onto the next step without further purification. Rf 0.61 (ethyl acetate/hexane 3:7); 1H NMR (300 MHz, CDCl3) δ 4.18 (dq, J=1.1, 7.2, 2H), 2.35-2.63 (m, 5H), 2.01-2.19 (m, 2H), 1.42-1.53 (m, 1H), 1.28 (t, J=7.2, 3H), 1.03 (d, J=6.4, 3H); 13C NMR (75 MHz, CDCl3) δ 208.9, 173.5, 60.6, 50.5, 42.7, 40.3, 33.4, 33.2, 19.0, 14.1; MS (EI) m/z 184 (M+, 23), 169 ([M-CH3]+, 3), 155 ([M-CH2CH3]+, 8), 139 ([M-OCH2CH3]+, 8), 128 (35), 111 (100), 99 (46). 55 (50); [α]D−46.9° (c=1.00, CH2Cl2). Analysis calc'd for C10H16O3: C, 65.19; H, 8.75. Found: C, 65.06; H, 8.73.

Provenance & Evidence