反应详情

温度

-78 °C

Compound E (0.19 mmol) was dissolved in anhydrous toluene (3 mL) and chilled to −78° C. DIBAL-H (0.585 mmol, 2.0 M in toluene) was added dropwise. The solution reacted for 45 minutes and was warmed slightly. The reaction was quenched with 10% aqueous sodium potassium tartrate. The layers were separated and the aqueous layer was extracted (3×20 mL) with ethyl acetate. The organic layers were combined, washed with brine (10 mL), dried, filtered and concentrated. Purification by flash chromatography (9:1 hexane/ethyl acetate) gave F in yields of 85-90%. 1H NMR (300 MHz, CDCl3): δ 0.8 (t, 3H), 1.25 (narrow m, 20H), 1.5 (s, 3H), 1.8 (narrow m, 2H), 4.0 (d, 2H), and 5.4 (t, 1H).

1. customThe solution reacted for 45 minutes
2. temperaturewas warmed slightly
3. customThe reaction was quenched with 10% aqueous sodium potassium tartrate
4. customThe layers were separated
5. extractionthe aqueous layer was extracted (3×20 mL) with ethyl acetate
6. washwashed with brine (10 mL)
7. customdried
8. filtrationfiltered
9. concentrationconcentrated
10. customPurification by flash chromatography (9:1 hexane/ethyl acetate)
11. customgave F
12. customin yields of 85-90%