Methyl 3-cyclopropyl-3-(4-chlorophenyl)propanoate → 3-Cyclopropyl-3-(4-chlorophenyl)propan-1-ol

Temperature

0 °C

A stirred solution of 10.7 grams (0.045 mole) of methyl 3-cyclopropyl-3-(4-chlorophenyl)propanoate in 45 ml of tetrahydrofuran was cooled to 0° C., and 45 ml of 1.0 M of lithium aluminum hydride in tetrahydrofuran was added slowly during a one hour period. Upon completion of addition, the reaction mixture was stirred at 0° C. for two hours and then was allowed to warm to ambient temperature. The reaction was quenched by the sequential addition of 2 ml of water, 2 ml of aqueous 15% sodium hydroxide, and 6 ml of water. The reaction mixture was taken up in 100 ml of diethyl ether. The solution was filtered, and the filtrate was dried with sodium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure, yielding 9.3 grams of 3-cyclopropyl-3-(4-chlorophenyl)propan-1-ol.

1. additionUpon completion of addition
2. temperatureto warm to ambient temperature
3. customThe reaction was quenched by the sequential addition of 2 ml of water, 2 ml of aqueous 15% sodium hydroxide, and 6 ml of water
4. filtrationThe solution was filtered
5. dry with materialthe filtrate was dried with sodium sulfate
6. filtrationThe mixture was filtered
7. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-ea1144f715a84f339a5cfe27b7831756

Source dataset

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05223536