反应详情

Lithium diisopropylamide (10.9 ml of 2.0M solution in heptane/tetrahydrofuran/ethylbenzene) was added to a stirred solution of tetrahydro-pyran-4-carboxylic acid methyl ester (3.00 g) in tetrahydrofuran (50 ml) at 0° C. under an atmosphere of nitrogen. The mixture was stirred for 30 minutes before dropwise addition of diiodomethane (2.51 ml). Stirring was continued for a further hour during which it warmed to room temperature. The reaction was poured into water (50 ml) and then extracted with diethyl ether (3×40 ml). The combined organics were washed with water (2×20 ml), 2M hydrochloric acid (20 ml), water (20 ml) and brine (20 ml). After drying (MgSO4), filtering and evaporating under reduced pressure a yellow oil was obtained which was purified by column chromatography eluting with 3:1 hexane/diethyl ether to give the title compound as a colourless oil (3.11 g, 53%).

1. waitwas continued for a further hour during which it
2. extractionextracted with diethyl ether (3×40 ml)
3. washThe combined organics were washed with water (2×20 ml), 2M hydrochloric acid (20 ml), water (20 ml) and brine (20 ml)
4. dry with materialAfter drying (MgSO4)
5. filtrationfiltering
6. customevaporating under reduced pressure a yellow oil
7. customwas obtained which
8. customwas purified by column chromatography
9. washeluting with 3:1 hexane/diethyl ether