Diethyl Ether → 6-Methoxy-1,1,4,7-tetramethyl-1,2-dihydronaphthalene

General Procedure A CeCl3 7 H2O (1.28 g, 3.4 mmol) was heated in an oil bath to 140-150° C. under high vacuum without stirring for 2 h, and then with stirring for 2 h. Argon was then introduced, and the flask was cooled to room temperature. Tetrahydrofuran (10 mL) was added, and the resulting slurry solution was stirred at room temperature under the argon atmosphere for 3 h. A solution of 7-methoxy-4,4,6-trimethyl-3,4-dihydro-2H-naphthalen-1-one (Compound 6, 0.53 g, 2.3 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 (1.2 mL, 3.4 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 IN NaHCO3, brine, dried over MgSO4, and filtered. The solvent was removed to give 0.42 g (80%) of the title compound as an orange oil.

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 3 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 IN NaHCO3, brine
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. customThe solvent was removed

ORD record

ord-cb14d780aade44b38cc4ceedc71cf8eb

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07026487B2