Diethyl Ether → HCID 10539589, compound

Participants

Reaction Steps

To a stirred solution of (1R,2R)-3-bromo-1,2-dicarbomethoxy-3-hydroxymethyl-cyclopropane (2.8 g, 10.5 mmol) in dichloromethane (120 ml) was added pyridinium chlorochromate (3.35 g, 15.7 mmol) and stirring continued over a period of 16 hours. Diethyl ether (120 ml) was added to the reaction mixture, which was then filtered with the aid of a Whatman glass microfibre filter and evaporated. Column chromatography of the crude product (diethyl ether/hexane 1:1) yielded (1R,2R)-3-bromo-1,2-dicarbomethoxy-3-formyl-cyclopropane (1.93 g, 69%) as a white solid. mp 52° C.; [α]20D=+108° (c=0.25 in MeOH): 1H NMR (CDCl3): d 3.16 (d, J=6.5 Hz, 1H), 3.27 (d, J=6.5 Hz, 1H), 3.76 (s, 3H), 3.83 (s. 3H), 9.26 (s, 1H). MS (EI) m/z 265, 267 [M+H+ ], 233, 235 (24) [M+ --OMe], 204, 206 (24), 176, 178 (44), 153 (100), 125 (95), 59 (69).

Provenance & Evidence