反应详情

(1-Diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (418 mg, 2.17 mmol) was added to a stirred suspension of 2,2-dimethyl-3-(tetrahydro-furan-3-yloxy)-propionaldehyde (250 mg, 1.45 mmol) and K2CO3 (601 mg, 4.35 mmol) in methanol (17.0 mL) at room temperature. After overnight stirring the bulk of the methanol was removed by rotary evaporation and the reaction mixture partitioned between ethyl ether and NaHCO3. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated to provide a crude liquid. Purification by flash column chromatography on silica gel using 30% ethyl acetate in hexanes followed by bulb to bulb distillation under reduced pressure provided 3-(2,2-dimethyl-but-3-ynyloxy)-tetrahydro-furan (169 mg, 69%) as a colorless liquid.

1. customwas removed by rotary evaporation
2. customthe reaction mixture partitioned between ethyl ether and NaHCO3
3. customThe organic layer was separated
4. washwashed with brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. customto provide a crude liquid
8. customPurification by flash column chromatography on silica gel using 30% ethyl acetate in hexanes
9. distillationfollowed by bulb to bulb distillation under reduced pressure