2-methoxycyclohexan-1-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2(S) 2-methoxycyclohexanone (4.089 g) and (3S,4R)-4-acetoxy-3[(R)-(t-butyldimethylsilyloxy)ethyl]azetidinone (4.63 g) in dichloromethane (140 ml) was prepared at -16°. Tin tetrachloride (14.3 g) was added dropwise via syringe at such a rate that the temperature was kept beetween -16° and -13°. The mixture was stirred for 10 minutes, then the temperature was increased to +3°. A solution of di-isopropylethylamine (5.33 g) dissolved in dichloromethane (40 ml) was added over 20 minutes. The reaction mixture was stirred for 10 minutes at +3°, then the reaction mixture was poured into 300 ml of a 1:1 mixture of sodium bicarbonate (saturated) and Rochelle's salt (saturated) and extracted into diethylether (500 ml) with vigorous stirring over 1 h. The organic layer was washed with saturated brine(150 ml), dried and the solvent removed to give an white solid (7.10 g). The crude solid was taken up in hot n-hexane (175 ml), filtered and the volume reduced to 75 ml. The resulting mixture was warmed to completely dissolve the solid. The resultant solution was cooled and stirred and the title compound was isolated by filtration as a white solid (3.03 g). was kept beetween -16° and -13° the temperature was increased to +3° was added over 20 minutes The reaction mixture was stirred for 10 minutes at +3° extracted into diethylether (500 ml) with vigorous stirring over 1 h The organic layer was washed with saturated brine(150 ml) dried the solvent removed

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-methoxycyclohexanone (39.0 mmol), hydroxylamine hydrochloride (72 mmol), and sodium acetate (48.8 mmol) in ethanol and water was heated at 70° C. overnight. Ethanol was removed, and the residue was dissolved in water and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried, and concentrated to give 1-(hydroxyimino)-2-methoxycyclohexane. Ethanol was removed the residue was dissolved in water The aqueous layer was extracted with ethyl acetate The combined organic layers were washed with brine dried concentrated

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2.5M n-butyllithium in hexane (13.2 ml, 33 mmol) at -78° C. was added diethyl ether (15 ml) followed by a solution of 3-bromopyridine (4.7 g, 30 mmol) in ether (90 ml) over a period of 10 minutes. After 1 hour at -78° C. a solution of (±)-2-methoxycyclohexanone (3.84 g, 30 mmol) in ether (20 ml) was added dropwise during 10 minutes. After 2 hours at -78° C. and 30 minutes at 0° C. the reaction mixture was warmed to 20° C. and then poured onto ice (150 g). The mixture was extracted with ether (2×50 ml) and then the combined organic extracts were extracted with 1N hydrochloric acid (50 ml). This aqueous extract was washed with ether (20 ml) and then treated with 2M sodium hydroxide solution (25 ml) and extracted with ether (3×100 ml). The organic extracts were combined, washed with brine then dried over anhydrous sodium sulphate Concentration in vacuo afforded (±)-2-methoxy-1-(pyrid-3-yl)cyclohexanol (5.0 g, 24 mmol) as a 4:1 mixture of cis and trans isomers; poured onto ice (150 g) The mixture was extracted with ether (2×50 ml) the combined organic extracts were extracted with 1N hydrochloric acid (50 ml) This aqueous extract was washed with ether (20 ml) treated with 2M sodium hydroxide solution (25 ml) extracted with ether (3×100 ml) washed with brine then dried over anhydrous sodium sulphate Concentration in vacuo

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-methoxycyclohexanone (39.0 mmol), hydroxylamine hydrochloride (72 mmol), and sodium acetate (48.8 mmol) in ethanol and water was heated at 70° C. overnight. Ethanol was removed, and the residue was dissolved in water and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried, and concentrated to give 1-(hydroxyimino)-2-methoxycyclohexane. Ethanol was removed the residue was dissolved in water The aqueous layer was extracted with ethyl acetate The combined organic layers were washed with brine dried concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add 5 ml dry MeOH to a flask under N2 containing indole (1 g, 8.5 mmol, 8.5 eq) and potassium hydroxide (202 mg, 3.59 mmol, 1 eq). Add to this solution 2-Methoxy-cyclohexanone (834 mg, 6.5 mmol, 6.5 eq). Heat reaction to 63° C. for 18 hours. Cool reaction and purify crude material by silica gel chromatography to give 442 mg (30% yield) of 3-(6-Methoxy-cyclohex-1-enyl)-1H-indole as a waxy yellow solid. Mass Spectrum (m/e): 228.02 (MH+). Heat reaction to 63° C. for 18 hours Cool reaction purify crude material by silica gel chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add 5 ml dry MeOH to a flask under N2 containing indole (1 g, 8.5 mmol, 8.5 eq) and potassium hydroxide (202 mg, 3.59 mmol, 1 eq). Add to this solution 2-Methoxy-cyclohexanone (834 mg, 6.5 mmol, 6.5 eq). Heat reaction to 63° C. for 18 hours. Cool reaction and purify crude material by silica gel chromatography to give 442 mg (30% yield) of 3-(6-Methoxy-cyclohex-1-enyl)-1H-indole as a waxy yellow solid. Mass Spectrum (m/e): 228.02 (MH+). Heat reaction to 63° C. for 18 hours Cool reaction purify crude material by silica gel chromatography