反应详情

温度

10 °C

To an ice cooled solution of 4-phenyl-1-butanol (20 g) and triethyl amine (15 g) in 200 ml of dichloromethane, a solution of methanesulfonyl chloride (12 ml) in 50 ml of dichloromethane was added dropwise. After stirring for 1 h at 10° C. the reaction mixture was washed with water. Extraction of the water phase with dichloromethane, drying of the combined organic phases over MgSO4 followed by removal of the volatile components in vacua, gave 29 g of a slightly yellow oil, 4-phenyl-1-butyl methanesulfonate, which was sufficiently pure for use in the next step. A mixture of spiro[isobenzofuran-1(3H),4′-piperidine] (2 g), 4-phenyl-1-butyl methanesulfonate (6 g) and potassium carbonate (14 g) in 75 ml of 4-methyl-2-pentanone was refluxed for 20 h. After cooling the reaction mixture was filtered and concentrated in vacuo. The remaining viscous oil was applied to a silica gel column (eluent: ether/methanol/triethyl amine 93:5:2) giving a colorless oil which crystallized as the fumarate salt, 2a. from acetone by addition of fumaric acid. Yield: 0.7 g, mp: 197-99° C.

1. washwas washed with water
2. extractionExtraction of the water phase with dichloromethane
3. dry with materialdrying of the combined organic phases over MgSO4
4. customfollowed by removal of the volatile components in vacua