Chlorotrimethylsilane → (1-Methyl-cyclohexyl)-acetic acid methyl ester

温度

0 °C

Step B To a suspension of CuI (7.61 g, 40 mmol) in anhydrous ethyl ether (20 mL) at 0° C. was added an ethyl ether solution (1.6 M) of MeLi (50 mL, 80 mmol) The reaction mixture was stirred at 0° C. for 10 min. The solvent was evaporated under reduced pressure, then dichloromethane (20 mL) was added under nitrogen at 0° C. The mixture was stirred for 5 min. The solvent was evaporated again. To the residue was added dichlormethane (20 mL), and the temperature of the mixture was lowered to −78° C. To the mixture was added chlorotrimethylsilane (4.3 g, 40 mmol) and a dichloromethane solution (20 mL) of cyclohexylidene-acetic acid methyl ester (3.1 g, 20 mmol). The reaction mixture was allowed to slowly warmed to 0° C. and stirred for 1 h. Aqueous saturated NH4Cl solution was added to quench the reaction. The mixture was extracted with ethyl ether twice. The organic layers were combined, dried over MgSO4, concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:5) to give (1-methyl-cyclohexyl)-acetic acid methyl ester as a colorless oil (3.3 g, 97%).

1. customThe solvent was evaporated under reduced pressure
2. additiondichloromethane (20 mL) was added under nitrogen at 0° C
3. stirringThe mixture was stirred for 5 min
4. customThe solvent was evaporated again
5. additionTo the residue was added dichlormethane (20 mL)
6. customwas lowered to −78° C
7. temperatureto slowly warmed to 0° C.
8. stirringstirred for 1 h
9. customto quench
10. customthe reaction
11. extractionThe mixture was extracted with ethyl ether twice
12. dry with materialdried over MgSO4
13. concentrationconcentrated
14. customThe residue was purified by chromatography (EtOAc:hexanes=1:5)

ORDレコード

ord-c2babd3dc8714f6c9337585d02633d15

出典データセット

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08354444B2