2-phenylmethoxypropan-1-ol

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

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromo-4-fluoro-benzaldehyde (30.0 g, 148 mmol), Na2CO3 (78.31 g, 738.8 mmol) and 2-benzyloxy propanol (24.56 g, 147.8 mmol) in anhydrous DMSO (300 mL) was heated with stirring at 130° C. (bath temp) for 72 h under N2. The reaction mixture was cooled to rt and diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O then brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (hexane to 30% EtOAc in hexane) to give the title compound: yield 3.84 g (7%). was heated The reaction mixture was cooled to rt extracted with EtOAc The organic layer was washed with H2O brine, dried (MgSO4) concentrated in vacuo The residue was purified by flash chromatography (hexane to 30% EtOAc in hexane)

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

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of ethyl 2-benzyloxylactate (9.5 g, 45.6 mmole) in anhydrous tetrahydrofuran (30 mL) was added dropwise during 30 minutes to a stirred solution of lithium aluminum hydride (1.06 g, 28 mmole) in anhydrous tetrahydrofuran (56 mL) at room temperature under argon atmosphere. Next, the mixture was stirred for 3 hours at 60° C. After cooling to 30° C., freshly prepared saturated solution of sodium sulfate (10 mL) was slowly added. The mixture was filtered and the solvent was distilled under reduced pressure. The residue was dissolved in dichloromethane (100 mL) and the solution was dried with anhydrous magnesium sulfate. The solvent then was distilled under reduced pressure. The residue was subjected to fractional vacuum distillation giving 6.2 g of colorless liquid product. NMR (d6-DMSO): 1.90 ppm (d, —CH3, 3H), 3.20-3.50 ppm (bm, —CH— and —CH2—, 3H), 4.53 ppm (s, —CH2—, 2H), 4.63 ppm (t, —OH, 1H), 7.33 ppm (m, 5H). After cooling to 30° C. The mixture was filtered the solvent was distilled under reduced pressure The residue was dissolved in dichloromethane (100 mL) the solution was dried with anhydrous magnesium sulfate The solvent then was distilled under reduced pressure The residue was subjected to fractional vacuum distillation

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromo-4-fluoro-benzaldehyde (30.0 g, 148 mmol), Na2CO3 (78.31 g, 738.8 mmol) and 2-benzyloxy propanol (24.56 g, 147.8 mmol) in anhydrous DMSO (300 mL) was heated with stirring at 130° C. (bath temp) for 72 h under N2. The reaction mixture was cooled to rt and diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O then brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (hexane to 30% EtOAc in hexane) to give the title compound: yield 3.84 g (7%). was heated The reaction mixture was cooled to rt extracted with EtOAc The organic layer was washed with H2O brine, dried (MgSO4) concentrated in vacuo The residue was purified by flash chromatography (hexane to 30% EtOAc in hexane)

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromo-4-fluoro-benzaldehyde (30.0 g, 148 mmol), Na2CO3 (78.31 g, 738.8 mmol) and 2-benzyloxy propanol (24.56 g, 147.8 mmol) in anhydrous DMSO (300 mL) was heated with stirring at 130° C. (bath temp) for 72 h under N2. The reaction mixture was cooled to rt and diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O then brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (hexane to 30% EtOAc in hexane) to give the title compound: yield 3.84 g (7%). was heated The reaction mixture was cooled to rt extracted with EtOAc The organic layer was washed with H2O brine, dried (MgSO4) concentrated in vacuo The residue was purified by flash chromatography (hexane to 30% EtOAc in hexane)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of ethyl 2-benzyloxylactate (9.5 g, 45.6 mmole) in anhydrous tetrahydrofuran (30 mL) was added dropwise during 30 minutes to a stirred solution of lithium aluminum hydride (1.06 g, 28 mmole) in anhydrous tetrahydrofuran (56 mL) at room temperature under argon atmosphere. Next, the mixture was stirred for 3 hours at 60° C. After cooling to 30° C., freshly prepared saturated solution of sodium sulfate (10 mL) was slowly added. The mixture was filtered and the solvent was distilled under reduced pressure. The residue was dissolved in dichloromethane (100 mL) and the solution was dried with anhydrous magnesium sulfate. The solvent then was distilled under reduced pressure. The residue was subjected to fractional vacuum distillation giving 6.2 g of colorless liquid product. NMR (d6-DMSO): 1.90 ppm (d, —CH3, 3H), 3.20–3.50 ppm (bm, —CH— and —CH2—, 3H), 4.53 ppm (s, —CH2—, 2H), 4.63 ppm (t, —OH, 1H), 7.33 ppm (m, 5H). After cooling to 30° C. The mixture was filtered the solvent was distilled under reduced pressure The residue was dissolved in dichloromethane (100 mL) the solution was dried with anhydrous magnesium sulfate The solvent then was distilled under reduced pressure The residue was subjected to fractional vacuum distillation

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromo-4-fluoro-benzaldehyde (30.0 g, 148 mmol), Na2CO3 (78.31 g, 738.8 mmol) and 2-benzyloxy propanol (24.56 g, 147.8 mmol) in anhydrous DMSO (300 mL) was heated with stirring at 130° C. (bath temp) for 72 h under N2. The reaction mixture was cooled to rt and diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O then brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (hexane to 30% EtOAc in hexane) to give the title compound: yield 3.84 g (7%). was heated The reaction mixture was cooled to rt extracted with EtOAc The organic layer was washed with H2O brine, dried (MgSO4) concentrated in vacuo The residue was purified by flash chromatography (hexane to 30% EtOAc in hexane)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of ethyl 2-benzyloxylactate (9.5 g, 45.6 mmole) in anhydrous tetrahydrofuran (30 mL) was added dropwise during 30 minutes to a stirred solution of lithium aluminum hydride (1.06 g, 28 mmole) in anhydrous tetrahydrofuran (56 mL) at room temperature under argon atmosphere. Next, the mixture was stirred for 3 hours at 60° C. After cooling to 30° C., freshly prepared saturated solution of sodium sulfate (10 mL) was slowly added. The mixture was filtered and the solvent was distilled under reduced pressure. The residue was dissolved in dichloromethane (100 mL) and the solution was dried with anhydrous magnesium sulfate. The solvent then was distilled under reduced pressure. The residue was subjected to fractional vacuum distillation giving 6.2 g of colorless liquid product. NMR (d6-DMSO): 1.90 ppm (d, —CH3, 3H), 3.20-3.50 ppm (bm, —CH— and —CH2—, 3H), 4.53 ppm (s, —CH2—, 2H), 4.63 ppm (t, —OH, 1H), 7.33 ppm (m, 5H). After cooling to 30° C. The mixture was filtered the solvent was distilled under reduced pressure The residue was dissolved in dichloromethane (100 mL) the solution was dried with anhydrous magnesium sulfate The solvent then was distilled under reduced pressure The residue was subjected to fractional vacuum distillation

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromo-4-fluoro-benzaldehyde (30.0 g, 148 mmol), Na2CO3 (78.31 g, 738.8 mmol) and 2-benzyloxy propanol (24.56 g, 147.8 mmol) in anhydrous DMSO (300 mL) was heated with stirring at 130° C. (bath temp) for 72 h under N2. The reaction mixture was cooled to rt and diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O then brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (hexane to 30% EtOAc in hexane) to give the title compound: yield 3.84 g (7%). was heated The reaction mixture was cooled to rt extracted with EtOAc The organic layer was washed with H2O brine, dried (MgSO4) concentrated in vacuo The residue was purified by flash chromatography (hexane to 30% EtOAc in hexane)