Methanol → HCID 21911993, compound

Participants

Reaction Conditions

Reaction Steps

Under inert atmosphere, 0.91 g (4.6 mmol) of TOSMIC in solution in anhydrous DME (4 ml) is added to 0.96 g (8.6 mmol) of potassium tert-butylate in suspension in 4 ml of anhydrous DME at −35° C. The reaction mixture is cooled to −50° C. then 1 g (4.4 mmol) of 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbaldehyde (Whitten J P, JOC 1986, 51 (10) 1891-1894) in solution in 4 ml of anhydrous DME is added dropwise, keeping the temperature below −45° C. The reaction mixture is stirred at this temperature for 30 min, then 11 ml of methanol is added, and the mixture is heated at 80° C. for 15 minutes. The solvents are concentrated under reduced pressure, and the residue is taken up in a water/acetic acid mixture (13 ml/0.5 ml), the aqueous phase is extracted with dichloromethane (3×100 ml), the organic phases are then washed with a saturated solution of NaHCO3, then dried over Na2SO4. After filtration, the filtrate is concentrated under reduced pressure and the residue is purified by filtration on basic alumina (eluent: A/B=DCM/AcEt 0 to 50% of B), 0.71 g of compound is thus obtained in the form of a yellowish orange oil. Yield=67%. MH+: 238 (Tr: 6.9 min, condition 1).

Provenance & Evidence