Potassium Cyanide → HCID 15238015, compound

A mixture of potassium cyanide (1.16 g) and 18-Crown-6 (registered trade mark, 236 mg) in acetonitrile (18 ml) was stirred for 15 min under an atmosphere of argon. To the mixture was added a solution of methyl [1-(2-bromoethyl)-1,2,3,4-tetrahydronaphthalen-5-yloxy]acetate (2.92 g) and tributylphosphine (1.99 g) in acetonitrile (10 ml). To the mixture was added dropwise a solution of carbon tetrachloride (0.95 ml) in acetonitrile (10 ml) under cooling with ice. The mixture was stirred overnight at room temperature. The mixture was diluted with ether, and the mixture was washed with 10% aqueous solution of citric acid. To this solution was added carbon tetrachloride (10 ml), and washed with water and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:9) to give the title compound (1.72 g) having the following physical data.

1. temperatureunder cooling with ice
2. stirringThe mixture was stirred overnight at room temperature
3. washthe mixture was washed with 10% aqueous solution of citric acid
4. additionTo this solution was added carbon tetrachloride (10 ml)
5. washwashed with water
6. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate
7. customevaporated
8. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:9)

ORD record

ord-19bd5b1c55d540f0a634313b31c39492

Source dataset

uspto-grants-1995_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05389666