HRID1795588

反应详情

EQUATION

反应方程式

HRID 1795588 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

1

PROCEDURE

实验过程

General Procedure F CeCl3.7H2O (2.6 g, 6.9 mmol) was heated in an oil bath at 140-150° C. under high vacuum without stirring for 1 h, and then with stirring for 2 h. Argon was then introduced, and the flask was cooled to room temperature. Tetrahydrofuran (15 mL) was added, and the resulting slurry solution was stirred at room temperature under the argon atmosphere for 16 h. A solution of 6-methoxy-4,4,7-trimethyl-3,4-dihydro-2H-naphthalen-1-one (Compound 30, 1.0 g, 4.6 mmol) and 5 mL of tetrahydrofuran was added, and the reaction mixture was stirred for 1 h, then cooled to 0° C. A solution of 3 M MeMgBr in diethyl ether (2.3 mL, 6.9 mmol) was added, and the ice bath was removed. After 1 h, the reaction was poured into concentrated sulfuric acid in ice, extracted with ethyl acetate, washed with NaHCO3 1 N, brine, dried over MgSO4, and filtered. The solvent was removed to give 1.0 g (100%) of the title compound as an orange oil. PNMR (300 MHz, CDCl3) δ 1.52 (s, 6 H), 2.28 (s, 3 H), 2.42 (d, 2 H, J=3.4 Hz), 2.49 (s, 1 H), 4.07 (s, 3 H), 5.86 (t, 1 H, J=2.5 Hz), 7.08 (s, 1 H), 7.30 (s, 1 H). 4-Ethyl-7-methoxy-1,1,6-trimethyl-1,2-dihydro-naphthalene (Compound 32)

WORKUP

后处理

  1. stirringwith stirring for 2 h
  2. additionArgon was then introduced
  3. stirringthe resulting slurry solution was stirred at room temperature under the argon atmosphere for 16 h
  4. stirringthe reaction mixture was stirred for 1 h
  5. temperaturecooled to 0° C
  6. customthe ice bath was removed
  7. waitAfter 1 h
  8. additionthe reaction was poured into concentrated sulfuric acid in ice
  9. extractionextracted with ethyl acetate
  10. washwashed with NaHCO3 1 N, brine
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. customThe solvent was removed