反应详情

温度

25 °C

To a suspension of 160.3 mg of sodium hydride (60% oil dispersion, 4.00 mmol) in 8 ml of THF at 0° C. was added a solution of dimethyl (S)-6-(tert-butyldimethylsilyloxy)-2-oxoheptylphosphonate 13 (1.41 g, 4.00 mmol) in 4 mL THF. The mixture was stirred at 0° C. for 30 min before a solution of aldehyde 7 (1.10 g, 2.65 mmol) in 4 ml of THF was added dropwise. The syringe containing the aldehyde was rinsed with 2 mL of THF to complete the addition and the mixture was stirred at 25° C. for 2.5 h. The reaction was worked up with addition of saturated aqueous ammonium chloride (50 mL) and the aqueous layer was extracted with ethyl acetate (2×75 mL). The ethyl acetate layers were combined and washed with brine, dried over 30 g of anhydrous sodium sulfate, filtered and concentrated in vacuo. FCC (flash column chromatography) purification (silica gel, 6:1 hex/EtOAc) provided 1.60 g (95%) of enone 14.

1. additionwas added dropwise
2. washwas rinsed with 2 mL of THF
3. additionthe addition
4. additionThe reaction was worked up with addition of saturated aqueous ammonium chloride (50 mL)
5. extractionthe aqueous layer was extracted with ethyl acetate (2×75 mL)
6. washwashed with brine
7. dry with materialdried over 30 g of anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customFCC (flash column chromatography) purification (silica gel, 6:1 hex/EtOAc)