2-(2-methoxyphenyl)cyclopentan-1-ol

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

Procedure: To a solution of 2-(2-methoxyphenyl)cyclopentanol (9.11 g, 47.4 mmol) in Acetone (Volume: 474 ml) was added Jones reagent (6.52 ml, 52.1 mmol) (8.0 M). After the addition was complete (the conversion of red reagent to green solid, and the supernatant solution took on the color of unreacted reagent), isopropanol was added to quench the excess reagent. The green solid was filtered off through ceilite and rinsed with acetone. The filtrate was concentrated and purified by flash chromatography to get 2-(2-methoxyphenyl)cyclopentanone (6.64 g, 34.9 mmol, 73.6% yield). LC-MS (M+H)+=191.0. 1H NMR (500 MHz, CD3OD) δ 7.24 (td, J=7.8, 1.8 Hz, 1H), 7.09 (dd, J=7.5, 1.7 Hz, 1H), 6.95 (d, J=8.2 Hz, 1H), 6.90 (td, J=7.4, 1.1 Hz, 1H), 3.77 (s, 3H), 3.43-3.37 (m, 1H), 2.48-2.30 (m, 3H), 2.23-2.11 (m, 2H), 2.00-1.88 (m, 1H). After the addition was added to quench the excess reagent The green solid was filtered off through ceilite rinsed with acetone The filtrate was concentrated purified by flash chromatography

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

Procedure: To a solution of (2-methoxyphenyl)magnesium bromide in THF (47.4 ml, 47.4 mmol) was added Copper(I) iodide (0.632 g, 3.32 mmol). The resulting solution was stirred at RT for 10 min. 6-oxabicyclo[3.1.0]hexane (4.11 ml, 47.4 mmol) was slowly added and the reaction mixture was stirred at RT overnight. Sat. NH4Cl was slowly added and the mixture was stirred at RT for 30 min. The product was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (SG, 0% to 60% EtOAc/Hex) to get 2-(2-methoxyphenyl)cyclopentanol (9.03 g, 47.0 mmol, 99% yield). LC-MS (M+Na)+=215.1. 1H NMR (500 MHz, CDCl3) δ 7.21 (t, J=5.8 Hz, 2H), 6.97 (t, J=7.3 Hz, 1H), 6.88 (d, J=8.2 Hz, 1H), 4.24 (q, J=5.9 Hz, 1H), 3.79 (s, 3H), 3.38-3.27 (m, 2H), 2.23-2.10 (m, 1H), 2.09-1.97 (m, 1H), 1.95-1.85 (m, 1H), 1.85-1.71 (m, 3H). the reaction mixture was stirred at RT overnight the mixture was stirred at RT for 30 min The product was extracted with CH2Cl2 The combined organic layers were washed with brine dried over Na2SO4 concentrated The residue was purified by flash chromatography (SG, 0% to 60% EtOAc/Hex)

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

Procedure: To a solution of (2-methoxyphenyl)magnesium bromide in THF (47.4 ml, 47.4 mmol) was added Copper(I) iodide (0.632 g, 3.32 mmol). The resulting solution was stirred at RT for 10 min. 6-oxabicyclo[3.1.0]hexane (4.11 ml, 47.4 mmol) was slowly added and the reaction mixture was stirred at RT overnight. Sat. NH4Cl was slowly added and the mixture was stirred at RT for 30 min. The product was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (SG, 0% to 60% EtOAc/Hex) to get 2-(2-methoxyphenyl)cyclopentanol (9.03 g, 47.0 mmol, 99% yield). LC-MS (M+Na)+=215.1. 1H NMR (500 MHz, CDCl3) δ 7.21 (t, J=5.8 Hz, 2H), 6.97 (t, J=7.3 Hz, 1H), 6.88 (d, J=8.2 Hz, 1H), 4.24 (q, J=5.9 Hz, 1H), 3.79 (s, 3H), 3.38-3.27 (m, 2H), 2.23-2.10 (m, 1H), 2.09-1.97 (m, 1H), 1.95-1.85 (m, 1H), 1.85-1.71 (m, 3H). the reaction mixture was stirred at RT overnight the mixture was stirred at RT for 30 min The product was extracted with CH2Cl2 The combined organic layers were washed with brine dried over Na2SO4 concentrated The residue was purified by flash chromatography (SG, 0% to 60% EtOAc/Hex)

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

Procedure: To a solution of 2-(2-methoxyphenyl)cyclopentanol (9.11 g, 47.4 mmol) in Acetone (Volume: 474 ml) was added Jones reagent (6.52 ml, 52.1 mmol) (8.0 M). After the addition was complete (the conversion of red reagent to green solid, and the supernatant solution took on the color of unreacted reagent), isopropanol was added to quench the excess reagent. The green solid was filtered off through ceilite and rinsed with acetone. The filtrate was concentrated and purified by flash chromatography to get 2-(2-methoxyphenyl)cyclopentanone (6.64 g, 34.9 mmol, 73.6% yield). LC-MS (M+H)+=191.0. 1H NMR (500 MHz, CD3OD) δ 7.24 (td, J=7.8, 1.8 Hz, 1H), 7.09 (dd, J=7.5, 1.7 Hz, 1H), 6.95 (d, J=8.2 Hz, 1H), 6.90 (td, J=7.4, 1.1 Hz, 1H), 3.77 (s, 3H), 3.43-3.37 (m, 1H), 2.48-2.30 (m, 3H), 2.23-2.11 (m, 2H), 2.00-1.88 (m, 1H). After the addition was added to quench the excess reagent The green solid was filtered off through ceilite rinsed with acetone The filtrate was concentrated purified by flash chromatography

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

Procedure: To a solution of 2-(2-methoxyphenyl)cyclopentanol (9.11 g, 47.4 mmol) in Acetone (Volume: 474 ml) was added Jones reagent (6.52 ml, 52.1 mmol) (8.0 M). After the addition was complete (the conversion of red reagent to green solid, and the supernatant solution took on the color of unreacted reagent), isopropanol was added to quench the excess reagent. The green solid was filtered off through ceilite and rinsed with acetone. The filtrate was concentrated and purified by flash chromatography to get 2-(2-methoxyphenyl)cyclopentanone (6.64 g, 34.9 mmol, 73.6% yield). LC-MS (M+H)+=191.0. 1H NMR (500 MHz, CD3OD) δ 7.24 (td, J=7.8, 1.8 Hz, 1H), 7.09 (dd, J=7.5, 1.7 Hz, 1H), 6.95 (d, J=8.2 Hz, 1H), 6.90 (td, J=7.4, 1.1 Hz, 1H), 3.77 (s, 3H), 3.43-3.37 (m, 1H), 2.48-2.30 (m, 3H), 2.23-2.11 (m, 2H), 2.00-1.88 (m, 1H). After the addition was added to quench the excess reagent The green solid was filtered off through ceilite rinsed with acetone The filtrate was concentrated purified by flash chromatography

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

Procedure: To a solution of (2-methoxyphenyl)magnesium bromide in THF (47.4 ml, 47.4 mmol) was added Copper(I) iodide (0.632 g, 3.32 mmol). The resulting solution was stirred at RT for 10 min. 6-oxabicyclo[3.1.0]hexane (4.11 ml, 47.4 mmol) was slowly added and the reaction mixture was stirred at RT overnight. Sat. NH4Cl was slowly added and the mixture was stirred at RT for 30 min. The product was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (SG, 0% to 60% EtOAc/Hex) to get 2-(2-methoxyphenyl)cyclopentanol (9.03 g, 47.0 mmol, 99% yield). LC-MS (M+Na)+=215.1. 1H NMR (500 MHz, CDCl3) δ 7.21 (t, J=5.8 Hz, 2H), 6.97 (t, J=7.3 Hz, 1H), 6.88 (d, J=8.2 Hz, 1H), 4.24 (q, J=5.9 Hz, 1H), 3.79 (s, 3H), 3.38-3.27 (m, 2H), 2.23-2.10 (m, 1H), 2.09-1.97 (m, 1H), 1.95-1.85 (m, 1H), 1.85-1.71 (m, 3H). the reaction mixture was stirred at RT overnight the mixture was stirred at RT for 30 min The product was extracted with CH2Cl2 The combined organic layers were washed with brine dried over Na2SO4 concentrated The residue was purified by flash chromatography (SG, 0% to 60% EtOAc/Hex)

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

Procedure: To a solution of (2-methoxyphenyl)magnesium bromide in THF (47.4 ml, 47.4 mmol) was added Copper(I) iodide (0.632 g, 3.32 mmol). The resulting solution was stirred at RT for 10 min. 6-oxabicyclo[3.1.0]hexane (4.11 ml, 47.4 mmol) was slowly added and the reaction mixture was stirred at RT overnight. Sat. NH4Cl was slowly added and the mixture was stirred at RT for 30 min. The product was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (SG, 0% to 60% EtOAc/Hex) to get 2-(2-methoxyphenyl)cyclopentanol (9.03 g, 47.0 mmol, 99% yield). LC-MS (M+Na)+=215.1. 1H NMR (500 MHz, CDCl3) δ 7.21 (t, J=5.8 Hz, 2H), 6.97 (t, J=7.3 Hz, 1H), 6.88 (d, J=8.2 Hz, 1H), 4.24 (q, J=5.9 Hz, 1H), 3.79 (s, 3H), 3.38-3.27 (m, 2H), 2.23-2.10 (m, 1H), 2.09-1.97 (m, 1H), 1.95-1.85 (m, 1H), 1.85-1.71 (m, 3H). the reaction mixture was stirred at RT overnight the mixture was stirred at RT for 30 min The product was extracted with CH2Cl2 The combined organic layers were washed with brine dried over Na2SO4 concentrated The residue was purified by flash chromatography (SG, 0% to 60% EtOAc/Hex)

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

Procedure: To a solution of 2-(2-methoxyphenyl)cyclopentanol (9.11 g, 47.4 mmol) in Acetone (Volume: 474 ml) was added Jones reagent (6.52 ml, 52.1 mmol) (8.0 M). After the addition was complete (the conversion of red reagent to green solid, and the supernatant solution took on the color of unreacted reagent), isopropanol was added to quench the excess reagent. The green solid was filtered off through ceilite and rinsed with acetone. The filtrate was concentrated and purified by flash chromatography to get 2-(2-methoxyphenyl)cyclopentanone (6.64 g, 34.9 mmol, 73.6% yield). LC-MS (M+H)+=191.0. 1H NMR (500 MHz, CD3OD) δ 7.24 (td, J=7.8, 1.8 Hz, 1H), 7.09 (dd, J=7.5, 1.7 Hz, 1H), 6.95 (d, J=8.2 Hz, 1H), 6.90 (td, J=7.4, 1.1 Hz, 1H), 3.77 (s, 3H), 3.43-3.37 (m, 1H), 2.48-2.30 (m, 3H), 2.23-2.11 (m, 2H), 2.00-1.88 (m, 1H). After the addition was added to quench the excess reagent The green solid was filtered off through ceilite rinsed with acetone The filtrate was concentrated purified by flash chromatography

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

Procedure: To a solution of (2-methoxyphenyl)magnesium bromide in THF (47.4 ml, 47.4 mmol) was added Copper(I) iodide (0.632 g, 3.32 mmol). The resulting solution was stirred at RT for 10 min. 6-oxabicyclo[3.1.0]hexane (4.11 ml, 47.4 mmol) was slowly added and the reaction mixture was stirred at RT overnight. Sat. NH4Cl was slowly added and the mixture was stirred at RT for 30 min. The product was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (SG, 0% to 60% EtOAc/Hex) to get 2-(2-methoxyphenyl)cyclopentanol (9.03 g, 47.0 mmol, 99% yield). LC-MS (M+Na)+=215.1. 1H NMR (500 MHz, CDCl3) δ 7.21 (t, J=5.8 Hz, 2H), 6.97 (t, J=7.3 Hz, 1H), 6.88 (d, J=8.2 Hz, 1H), 4.24 (q, J=5.9 Hz, 1H), 3.79 (s, 3H), 3.38-3.27 (m, 2H), 2.23-2.10 (m, 1H), 2.09-1.97 (m, 1H), 1.95-1.85 (m, 1H), 1.85-1.71 (m, 3H). the reaction mixture was stirred at RT overnight the mixture was stirred at RT for 30 min The product was extracted with CH2Cl2 The combined organic layers were washed with brine dried over Na2SO4 concentrated The residue was purified by flash chromatography (SG, 0% to 60% EtOAc/Hex)