Methanol → HCID 57166467, compound

Temperature

-78 °C

1 ml of dry ether was added to 141 mg of copper (I) iodide in a stream of nitrogen gas, and 1.35 ml of ether solution (1.1M) of a methyllithium was added dropwise to the mixture while cooling it by ice. The mixture was cooled down to -78° C. To the reaction mixture was added a solution of (1S, 2R)-2-chloroformyl-1-methoxycarbonylcyclohex-4-ene (50 mg) prepared by a method similar to that of Example 1 in ether (0.5 ml) at -70° C., and the mixture was stirred for one hour. After addition of methanol, the mixture was allowed to stand to return to room temperature, a saturated ammonium chloride solution was then added, and the mixture was stirred for 30 minutes. The reaction mixture was extracted with ether, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=15:85) to be purified, and thus 35 mg of the titled compound was obtained.

1. additionwas added dropwise to the mixture
2. temperaturewhile cooling it by ice
3. customto return to room temperature
4. stirringthe mixture was stirred for 30 minutes
5. extractionThe reaction mixture was extracted with ether
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated
8. customto be purified

ORD record

ord-1173bd097c56403fb675d931af43f02f

Source dataset

uspto-grants-1994_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05329042