HRID627579

反应详情

EQUATION

反应方程式

HRID 627579 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

1

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

A solution of compound 3 (10.85 g; 29 mmol) in dry THF (100 mL) kept in an ice bath was treated with a solution of 1M lithium hydroxide (100 mL) and stirred for 4 h at 0° C. until the starting material disappeared (as shown by TLC). The solvent was removed and the residue was diluted with water (25 mL). The pH of the aqueous solution was adjusted to ˜2 with 5% HCl and the solution was extracted with ethyl acetate (2×250 mL) and washed with brine (100 mL). The organic extract was dried over anhydrous sodium sulfate, filtered and concentrated, yielding a crude product which was purified by flash chromatography (silica gel; hexane/ethyl acetate 50:50) to give 4 as a white solid (8.8 g; 84% yield). 1H NMR (DMSO-d6) δ 8.1 (s, 1H), 7.5 (s, 1H), 7.3 (m, 5H), 5.0 (s, 2H), 4.4 (m, 1H), 4.2 (m, 1H), 2.8 (s, 1H), 2.5 (m, 1H), 2.4 (m, 1H), 1.6 (m, 2H), 1.4 (m, 1H), 0.8 (d, 6H)

WORKUP

后处理

  1. customThe solvent was removed
  2. additionthe residue was diluted with water (25 mL)
  3. extractionthe solution was extracted with ethyl acetate (2×250 mL)
  4. washwashed with brine (100 mL)
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customyielding a crude product which
  10. customwas purified by flash chromatography (silica gel; hexane/ethyl acetate 50:50)