1-(4-chlorophenyl)-2-cyclopropylethanone

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

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

Conditions: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Crude 1-(4-chlorophenyl)-2-cyclopropylethanone (from the previous reaction) in dry dimethylformamide (150 ml) was added dropwise to a stirred suspension of hexane-washed sodium hydride (4.57 g of a 60% dispersion in oil, 114 mmol) in dry dimethylformamide (35 ml) under nitrogen. After 1 hour the mixture was cooled to -30° C. and iodomethane (16.2 g, 114 mmol) in dry dimethylformamide (35 ml) added very slowly. The mixture was then poured into water and the resultant mixture extracted with ether. The extracts were washed with brine, dried and evaporated in vacuo. Chromatography [SiO2, hexane-ethyl acetate (95:5)] gave 1-(4-chlorophenyl)-2-cyclopropylpropan-1-one (7.66 g, approximately 70% pure, approximately 28% based on 1-(4-chlorophenyl)-2-cyclopropylethanol). washed sodium hydride (4.57 g of a 60% dispersion in oil, 114 mmol) in dry dimethylformamide (35 ml) under nitrogen the resultant mixture extracted with ether The extracts were washed with brine dried evaporated in vacuo

Conditions: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Crude 1-(4-chlorophenyl)-2-cyclopropylethanone (from the previous reaction) in dry dimethylformamide (150 ml) was added dropwise to a stirred suspension of hexane-washed sodium hydride (4.57 g of a 60% dispersion in oil, 114 mmol) in dry dimethylformamide (35 ml) under nitrogen. After 1 hour the mixture was cooled to -30° C. and iodomethane (16.2 g, 114 mmol) in dry dimethylformamide (35 ml) added very slowly. The mixture was then poured into water and the resultant mixture extracted with ether. The extracts were washed with brine, dried and evaporated in vacuo. Chromatography [SiO2, hexane-ethyl acetate (95:5)] gave 1-(4-chlorophenyl)-2-cyclopropylpropan-1-one (7.66 g, approximately 70% pure, approximately 28% based on 1-(4-chlorophenyl)-2-cyclopropylethanol). washed sodium hydride (4.57 g of a 60% dispersion in oil, 114 mmol) in dry dimethylformamide (35 ml) under nitrogen the resultant mixture extracted with ether The extracts were washed with brine dried evaporated in vacuo

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

Procedure: Oxalyl chloride (14.3 ml, 160 mmol) was added dropwise to a stirred solution of dimethylsulphoxide (14.3 ml, 200 mmol) in dry dichloromethane (350 ml) at -78° C. After 15 minutes 1-(4-chlorophenyl)-2-cyclopropylethanol (12.98 g, 66 mmol) in dry dichloromethane (120 ml) was added to the mixture. After an hour triethylamine (71.4 ml), 510 mmol) was added and the mixture warmed to room temperature and poured into water. The mixture was extracted with dichloromethane and the combined extracts washed with water, dried and evaporated in vacuo to give crude 1-(4-chlorophenyl)-2-cyclopropylethanone which was used without further purification. The mixture was extracted with dichloromethane the combined extracts washed with water dried evaporated in vacuo

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

Procedure: Oxalyl chloride (5.5 ml, 63 mmol) was added dropwise to a stirred solution of dimethylsulphoxide (5.5 ml, 78 mmol) in dry dichloromethane (150 ml) at -78° C. After 15 minutes 1-(4-chlorophenyl)-2-cyclopropylethanol (5.00 g, 25.4 mmol) in dry dichloromethane (60 ml) was added to the mixture. After an hour triethylamine (27.5 ml, 197 mmol) was added, the mixture warmed to room temperature and poured into water. The mixture was extracted with dichloromethane and the extracts washed with water, dried and evaporated in vacuo to give crude 1-(4-chlorophenyl)-2-cyclopropylethanone which was used without further purification. The mixture was extracted with dichloromethane the extracts washed with water dried evaporated in vacuo

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

Procedure: Oxalyl chloride (5.5 ml, 63 mmol) was added dropwise to a stirred solution of dimethylsulphoxide (5.5 ml, 78 mmol) in dry dichloromethane (150 ml) at -78° C. After 15 minutes 1-(4-chlorophenyl)-2-cyclopropylethanol (5.00 g, 25.4 mmol) in dry dichloromethane (60 ml) was added to the mixture. After an hour triethylamine (27.5 ml, 197 mmol) was added, the mixture warmed to room temperature and poured into water. The mixture was extracted with dichloromethane and the extracts washed with water, dried and evaporated in vacuo to give crude 1-(4-chlorophenyl)-2-cyclopropylethanone which was used without further purification. The mixture was extracted with dichloromethane the extracts washed with water dried evaporated in vacuo

Conditions: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Crude 1-(4-chlorophenyl)-2-cyclopropylethanone (from the previous reaction) in dry dimethylformamide (150 ml) was added dropwise to a stirred suspension of hexane-washed sodium hydride (4.57 g of a 60% dispersion in oil, 114 mmol) in dry dimethylformamide (35 ml) under nitrogen. After 1 hour the mixture was cooled to -30° C. and iodomethane (16.2 g, 114 mmol) in dry dimethylformamide (35 ml) added very slowly. The mixture was then poured into water and the resultant mixture extracted with ether. The extracts were washed with brine, dried and evaporated in vacuo. Chromatography [(SiO2, hexane-ethyl acetate (95:5)] gave 1-(4-chlorophenyl)-2-cyclopropylpropan-1-one (7.66 g, approximately 70% pure, approximately 28% based on 1-(4-chlorophenyl)-2-cyclopropylethanol). washed sodium hydride (4.57 g of a 60% dispersion in oil, 114 mmol) in dry dimethylformamide (35 ml) under nitrogen the resultant mixture extracted with ether The extracts were washed with brine dried evaporated in vacuo

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

Procedure: Oxalyl chloride (14.3 ml, 160 mmol) was added dropwise to a stirred solution of dimethylsulphoxide (14.3 ml, 200 mmol) in dry dichloro-methane methane (350 ml) at -78° C. After 15 minutes 1-(4-chlorophenyl)-2-cyclopropylethanol (12.98 g, 66 mmol) in dry dichloromethane (120 ml) was added to the mixture. After an hour triethylamine (71.4 ml), 510 mmol) was added and the mixture warmed to room temperature and poured into water. The mixture was extracted with dichloromethane and the combined extracts washed with water, dried and evaporated in vacuo to give crude 1-(4-chlorophenyl)-2-cyclopropylethanone which was used without further purification. The mixture was extracted with dichloromethane the combined extracts washed with water dried evaporated in vacuo

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

Procedure: Oxalyl chloride (14.3 ml, 160 mmol) was added dropwise to a stirred solution of dimethylsulphoxide (14.3 ml, 200 mmol) in dry dichloro-methane methane (350 ml) at -78° C. After 15 minutes 1-(4-chlorophenyl)-2-cyclopropylethanol (12.98 g, 66 mmol) in dry dichloromethane (120 ml) was added to the mixture. After an hour triethylamine (71.4 ml), 510 mmol) was added and the mixture warmed to room temperature and poured into water. The mixture was extracted with dichloromethane and the combined extracts washed with water, dried and evaporated in vacuo to give crude 1-(4-chlorophenyl)-2-cyclopropylethanone which was used without further purification. The mixture was extracted with dichloromethane the combined extracts washed with water dried evaporated in vacuo

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

Procedure: Oxalyl chloride (5.5 ml, 63 mmol) was added dropwise to a stirred solution of dimethylsulphoxide (5.5 ml, 78 mmol) in dry dichloro-methane (150 ml) at -78° C. After 15 minutes 1-(4-chlorophenyl)-2-cyclopropylethanol (5.00 g, 25.4 mmol) in dry dichloromethane (60 ml) was added to the mixture. After an hour triethylamine (27.5 ml, 197 mmol) was added, the mixture warmed to room temperature and poured into water. The mixture was extracted with dichloromethane and the extracts washed with water, dried and evaporated in vacuo to give crude 1-(4-chlorophenyl)-2-cyclopropylethanone which was used without further purification. The mixture was extracted with dichloromethane the extracts washed with water dried evaporated in vacuo

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