ethyl 2-cyclohexyloxyacetate

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

Procedure: To a solution of NaOH (4.89 g, 122 mmol) in a mixture of water (20 mL) and MeOH (20 mL) in an ice bath was added a solution of ethyl 2-(cyclohexyloxy)acetate (3.8 g, 20.4 mmol) in MeOH (10 mL) slowly and the mixture was stirred at rt for 2 h. It was then acidified to pH 4 with concentrated hydrochloric acid and extracted with DCM (20 mL×2). The combined organic layers were washed with brine (40 mL×2), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc) to give the title compound as pale yellow oil (2.7 g, 84%). extracted with DCM (20 mL×2) The combined organic layers were washed with brine (40 mL×2) dried over anhydrous Na2SO4 concentrated in vacuo The residue was purified by a silica gel column chromatography (EtOAc)

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

Procedure: To a mixture of cyclohexanol (2.40 g, 24.0 mmol) and Rh2(OAc)4 (50 mg, 0.11 mmol) in DCM (50 mL) was added ethyl 2-diazoacetate (2.73 g, 23.9 mmol) and the mixture was stirred at rt for 5 min. It was then filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=15:1) to give the title compound as colorless oil (3.8 g, 85%). It was then filtered the filtrate was concentrated in vacuo The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=15:1)

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

Procedure: To a solution of NaOH (4.89 g, 122 mmol) in a mixture of water (20 mL) and MeOH (20 mL) in an ice bath was added a solution of ethyl 2-(cyclohexyloxy)acetate (3.8 g, 20.4 mmol) in MeOH (10 mL) slowly and the mixture was stirred at rt for 2 h. It was then acidified to pH 4 with concentrated hydrochloric acid and extracted with DCM (20 mL×2). The combined organic layers were washed with brine (40 mL×2), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc) to give the title compound as pale yellow oil (2.7 g, 84%). extracted with DCM (20 mL×2) The combined organic layers were washed with brine (40 mL×2) dried over anhydrous Na2SO4 concentrated in vacuo The residue was purified by a silica gel column chromatography (EtOAc)

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

Procedure: To a mixture of cyclohexanol (2.40 g, 24.0 mmol) and Rh2(OAc)4 (50 mg, 0.11 mmol) in DCM (50 mL) was added ethyl 2-diazoacetate (2.73 g, 23.9 mmol) and the mixture was stirred at rt for 5 min. It was then filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=15:1) to give the title compound as colorless oil (3.8 g, 85%). It was then filtered the filtrate was concentrated in vacuo The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=15:1)

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

Procedure: To a solution of cyclohexanol (1.0 g, 0.95 mmol) in dichloromethane (30 mL) is added rhodium (II) acetate dimer (44 mg) followed by ethyl diazoacetate (1.14 g, 10.0 mmol). The reaction mixture is stirred at RT for 20 min. The reaction mixture is diluted with Et2O, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 1.57 g of the product 407. 1H NMR (CDCl3) δ 4.23 (q, 2H), 4.10 (s, 2H), 3.33 (m, 1H), 1.93 (m, 2H), 1.74 (m, 2H), 1.54 (m, 1H), 1.4-1.1 (m, 8H) filtered through Celite the filtrate is evaporated distilled at 150° C.

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

Procedure: To a solution of NaOH (4.89 g, 122 mmol) in a mixture of water (20 mL) and MeOH (20 mL) in an ice bath was added a solution of ethyl 2-(cyclohexyloxy)acetate (3.8 g, 20.4 mmol) in MeOH (10 mL) slowly and the mixture was stirred at rt for 2 h. It was then acidified to pH 4 with concentrated hydrochloric acid and extracted with DCM (20 mL×2). The combined organic layers were washed with brine (40 mL×2), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc) to give the title compound as pale yellow oil (2.7 g, 84%). extracted with DCM (20 mL×2) The combined organic layers were washed with brine (40 mL×2) dried over anhydrous Na2SO4 concentrated in vacuo The residue was purified by a silica gel column chromatography (EtOAc)

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

Procedure: To a mixture of cyclohexanol (2.40 g, 24.0 mmol) and Rh2(OAc)4 (50 mg, 0.11 mmol) in DCM (50 mL) was added ethyl 2-diazoacetate (2.73 g, 23.9 mmol) and the mixture was stirred at rt for 5 min. It was then filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=15:1) to give the title compound as colorless oil (3.8 g, 85%). It was then filtered the filtrate was concentrated in vacuo The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=15:1)

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

Procedure: To a solution of cyclohexanol (1.0 g, 0.95 mmol) in dichloromethane (30 mL) is added rhodium (II) acetate dimer (44 mg) followed by ethyl diazoacetate (1.14 g, 10.0 mmol). The reaction mixture is stirred at RT for 20 min. The reaction mixture is diluted with Et2O, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 1.57 g of the product 407. 1H NMR (CDCl3) δ 4.23 (q, 2H), 4.10 (s, 2H), 3.33 (m, 1H), 1.93 (m, 2H), 1.74 (m, 2H), 1.54 (m, 1H), 1.4-1.1 (m, 8H) filtered through Celite the filtrate is evaporated distilled at 150° C.

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

Procedure: To a solution of cyclohexanol (1.0 g, 0.95 mmol) in dichloromethane (30 mL) is added rhodium (II) acetate dimer (44 mg) followed by ethyl diazoacetate (1.14 g, 10.0 mmol). The reaction mixture is stirred at RT for 20 min. The reaction mixture is diluted with Et2O, filtered through celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 1.57 g of the product 407. 1H NMR (CDCl3) δ 4.23 (q, 2H), 4.10 (s, 2H), 3.33 (m, 1H), 1.93 (m, 2H), 1.74 (m, 2H), 1.54 (m, 1H), 1.4-1.1 (m, 8H) filtered through celite the filtrate is evaporated distilled at 150° C.

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

Procedure: To a solution of cyclohexanol (1.0 g, 0.95 mmol) in dichloromethane (30 mL) is added rhodium (II) acetate dimer (44 mg) followed by ethyl diazoacetate (1.14 g, 10.0 mmol). The reaction mixture is stirred at RT for 20 min. The reaction mixture is diluted with Et2O, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 1.57 g of the product 407. 1H NMR (CDCl3) δ 4.23 (q, 2H), 4.10 (s, 2H), 3.33 (m, 1H), 1.93 (m, 2H), 1.74 (m, 2H), 1.54 (m, 1H), 1.4-1.1 (m, 8H) filtered through Celite the filtrate is evaporated distilled at 150° C.