methyl 3-phenylbutanoate

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: n-Butyllithium (2.5 M hexanes 12.4 ml, 30.9 mmol) is added to N,N-diisopropylamine (4.4 ml, 31.4 mmol) in tetrahydrofuran (THF, 50 ml) at 0° C. After 10 minutes, the resultant solution is transferred via cannula to a cooled (−78° C.) solution of methyl 3-phenylbutyrate (5.0 g, 28.05 mmol) in THF (50 ml). After 40 minutes, the resultant solution is transferred via cannula to a solution of acetyl chloride (19.15 ml) in THF (50 ml). The resultant mixture is stirred at −78° C. for 1.5 hours, then warmed to 0° C. after which water is added and the mixture is then poured into saturated NaHCO3 and extracted with EtOAc. The combined organic phases are washed with brine, dried (MgSO4) and evaporated. Purification by flash chromatography (12:1 EtOAc-hexane elution) affords the title compound. δH 1.3 (d J 7 3H), 2.3 (s 3H), 3.4 (s 3H), 3.6 (m 1H), 3.8 (m 1H), 7.2-7.4 (m 5H) After 40 minutes is added extracted with EtOAc The combined organic phases are washed with brine dried (MgSO4) evaporated Purification by flash chromatography (12:1 EtOAc-hexane elution)

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

Procedure: Thionyl chloride (44 ml, 91.4 mmol) is added dropwise to methanol (30 ml) at 0° C., followed by 3-phenylbutyric acid (10 g, 60.9 mmol). The reaction is stirred for 4 hours and the solvent is evaporated. The residue is partitioned between t-butylnethyl ether and aqueous ammonia. The organic phase is washed with water and brine, dried (Na2SO4) and evaporated to afford the title compound. MH+179. the solvent is evaporated The residue is partitioned between t-butylnethyl ether and aqueous ammonia The organic phase is washed with water and brine dried (Na2SO4) evaporated

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: n-Butyllithium (2.5 M hexanes 12.4 ml, 30.9 mmol) is added to N,N-diisopropylamine (4.4 ml, 31.4 mmol) in tetrahydrofuran (THF, 50 ml) at 0° C. After 10 minutes, the resultant solution is transferred via cannula to a cooled (−78° C.) solution of methyl 3-phenylbutyrate (5.0 g, 28.05 mmol) in THF (50 ml). After 40 minutes, the resultant solution is transferred via cannula to a solution of acetyl chloride (19.15 ml) in THF (50 ml). The resultant mixture is stirred at −78° C. for 1.5 hours, then warmed to 0° C. after which water is added and the mixture is then poured into saturated NaHCO3 and extracted with EtOAc. The combined organic phases are washed with brine, dried (MgSO4) and evaporated. Purification by flash chromatography (12:1 EtOAc-hexane elution) affords the title compound. δH 1.3 (d J 7 3H), 2.3 (s 3H), 3.4 (s 3H), 3.6 (m 1H), 3.8 (m 1H), 7.2-7.4 (m 5H) After 40 minutes is added extracted with EtOAc The combined organic phases are washed with brine dried (MgSO4) evaporated Purification by flash chromatography (12:1 EtOAc-hexane elution)

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

Procedure: Thionyl chloride (44 ml, 91.4 mmol) is added dropwise to methanol (30 ml) at 0° C., followed by 3-phenylbutyric acid (10 g, 60.9 mmol). The reaction is stirred for 4 hours and the solvent is evaporated. The residue is partitioned between t-butylnethyl ether and aqueous ammonia. The organic phase is washed with water and brine, dried (Na2SO4) and evaporated to afford the title compound. MH+179. the solvent is evaporated The residue is partitioned between t-butylnethyl ether and aqueous ammonia The organic phase is washed with water and brine dried (Na2SO4) evaporated

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

Procedure: n-Butyllithium (2.5 M hexanes 12.4 ml, 30.9 mmol) is added to N,N-diisopropylamine (4.4 ml, 31.4 mmol) in tetrahydrofuran (THF, 50 ml) at 0° C. After 10 minutes, the resultant solution is transferred via cannula to a cooled (−78° C.) solution of methyl 3-phenylbutyrate (5.0 g, 28.05 mmol) in THF (50 ml). After 40 minutes, the resultant solution is transferred via cannula to a solution of acetyl chloride (19.15 ml) in THF (50 ml). The resultant mixture is stirred at −78° C. for 1.5 hours, then warmed to 0° C. after which water is added and the mixture is then poured into saturated NaHCO3 and extracted with EtOAc. The combined organic phases are washed with brine, dried (MgSO4) and evaporated. Purification by flash chromatography (12:1 EtOAc-hexane elution) affords the title compound. δH 1.3 (d J 7 3H), 2.3 (s 3H), 3.4 (s 3H), 3.6 (m 1H), 3.8 (m 1H), 7.2-7.4 (m 5H) After 40 minutes is added extracted with EtOAc The combined organic phases are washed with brine dried (MgSO4) evaporated Purification by flash chromatography (12:1 EtOAc-hexane elution)

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

Procedure: Thionyl chloride (44 ml, 91.4 mmol) is added dropwise to methanol (30 ml) at 0° C., followed by 3-phenylbutyric acid (10 g, 60.9 mmol). The reaction is stirred for 4 hours and the solvent is evaporated. The residue is partitioned between t-butylnethyl ether and aqueous ammonia. The organic phase is washed with water and brine, dried (Na2SO4) and evaporated to afford the title compound. MH+179. the solvent is evaporated The residue is partitioned between t-butylnethyl ether and aqueous ammonia The organic phase is washed with water and brine dried (Na2SO4) evaporated