Carbon Dioxide → HCID 18786121, compound

Participants

Reaction Steps

51.82 ml of a 1.5 molar solution of DIBAL-H in toluene are added dropwise to a solution, cooled to -78° C. with a bath of solid carbon dioxide and acetone, of 10 g (35.3 mmol) of 2-ethyloxycarbonyl-3-methyl-7-bromobenzofuran in 100 ml of toluene. The solution is allowed to return to room temperature and 50 ml of water and 100 ml of a saturated solution of Rochelle salt are successively added. Extraction is carried out with ethyl acetate (3×80 ml). The organic phases are combined, dried over magnesium sulphate and concentrated. The residue is purified by silica column chromatography (elution solvent: 2% methanol in dichloromethane). 6.3 g (Yield: 74%) of 2-hydroxymethyl-3-methyl-7-bromobenzofuran are obtained--M.p.: 103° C.

Provenance & Evidence