dicyclohexylmethanone

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the procedures of Example 15, 9.7 g. (0.05 mole) of dicyclohexyl ketone and 14.4 g. (0.1 mole) of cyclopropyl magnesium bromide in dry tetrahydrofuran were reacted and the resulting carbinol dissolved in glacial acetic acid was treated with hydrogen bromide to give 4,4-dicyclohexyl-3-butenyl bromide, b.p. 168°-171° C. (0.1 mm.).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the procedures of Example 15, 9.7 g. (0.05 mole) of dicyclohexyl ketone and 14.4 g. (0.1 mole) of cyclopropyl magnesium bromide in dry tetrahydrofuran were reacted and the resulting carbinol dissolved in glacial acetic acid was treated with hydrogen bromide to give 4,4-dicyclohexyl-3-butenyl bromide, b.p. 168°-171° C. (0.1 mm.).

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To an ice-cooled solution of 1-(3-cyanobenzyl)-4-(2-methoxyphenyl)piperazine (5.60 g, 18.2 mmol) in 250 mL of tetrahydrofuran was added a solution of cyclohexylmagnesium chloride in ethyl ether (27.3 mL, 2.0M) under nitrogen. The solution was slowly warmed to 25° C. and then brought to reflux. After 48 h of reflux, thin layer chromatography indicated that the reaction was complete. The reaction mixture was then cooled to 0° C., ice cold 6N HCl solution (200 mL) was added, and the reaction mixture was stirred at ambient temperature for 3 h. The reaction mixture was then poured into a separatory funnel and washed with ether. The aqueous layer was then basified with K2CO3 and then extracted with chloroform. The organic extracts were combined, dried (Na2SO4), and concentrated to provide a dark green-brown oil. This material was purified on flash silica gel (1% methanol-chloroform) to afford 7.88 g (quantitative yield) of expected cyclohexyl ketone as a brown oil whose 1H NMR in CDCl3 was consistent with the desired structure. to reflux After 48 h of reflux The reaction mixture was then cooled to 0° C. The reaction mixture was then poured into a separatory funnel washed with ether extracted with chloroform dried (Na2SO4) concentrated to provide a dark green-brown oil This material was purified on flash silica gel (1% methanol-chloroform)

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,1-Dimethylethyl 4-(triphenylmethyl)-1-piperazine carboxylate (1.0 g, 2.3 mmol) and tetramethylethylenediamine (1.0 g, 8.6 mmol) were dissolved in tetrahydrofuran (10 mL), which was cooled to −78° C. A 1.0 M solution of sec-butyllithium in hexane and cyclohexane (7.2 mL, 7.2 mmol) was added thereto, and the mixture was stirred for 2 hours and the temperature was elevated to −50° C. After cooling to −78° C. again, a solution of dicyclohexyl ketone (1.1 g, 5.9 mmol) in tetrahydrofuran (10 mL) was added dropwise thereto, and the mixture was stirred for 15 hours while elevating the temperature to room temperature. To the reaction solution was added an aqueous saturated ammonium chloride solution, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=7:3) to obtain the title compound (0.95 g, yield 74%). was elevated to −50° C After cooling to −78° C. again the mixture was stirred for 15 hours to room temperature the resulting mixture was extracted with ethyl acetate The extract was washed with water concentrated under reduced pressure The residue was purified with silica gel column chromatography (hexane:ethyl acetate=7:3)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the procedures of Example 15, 9.7 g. (0.05 mole) of dicyclohexyl ketone and 14.4 g. (0.1 mole) of cyclopropyl magnesium bromide in dry tetrahydrofuran were reacted and the resulting carbinol dissolved in glacial acetic acid was treated with hydrogen bromide to give 4,4-dicyclohexyl-3-butenyl bromide, b.p. 168°-171° C. (0.1 mm.).