Cyclohexane, (bromomethyl)- → Methyl 3-cyclohexyl-2-methyl-2-phenylpropanate

温度

25 °C

A solution of 2-phenyl-propionic acid methyl ester (3.0 g, 18.27 mmol) in tetrahydrofuran (25 mL) at −78° C. was treated dropwise with the lithium hexamethyldisilazide (21.9 mL, 1M in tetrahydrofuran, 21.9 mmol) and stirred for 1 hour. Bromomethyl-cyclohexane (3.09 mL, 21.92 mmol) was added to the reaction and the reaction was allowed to warm to 25° C. and stirred for 18 hours. The solvent was removed in vacuo and the residue was partitioned between water and ethyl acetate. The aqueous phase was extracted three times with ethyl acetate and the ethyl acetate layers were combined, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane, then 2.5% ethyl acetate in hexane, and 5% ethyl acetate in hexane to give the title compound (4.02 g, 84%). 1H NMR (300 MHz, CDCl3): δ ppm 1.11 (m, 10H) 1.55 (m, 4H) 1.80 (m, 1H) 2.04 (m, 1H) 3.64 (m, 3H) 7.29 (m, 5H).

1. stirringstirred for 18 hours
2. customThe solvent was removed in vacuo
3. customthe residue was partitioned between water and ethyl acetate
4. extractionThe aqueous phase was extracted three times with ethyl acetate
5. dry with materialdried with sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was chromatographed on silica gel eluting with hexane

ORDレコード

ord-ddfb2fe1ac2648dd89fd37fd398aae52

出典データセット

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07538105B2