(1R)-1-phenylpropane-1,3-diol

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

Procedure: To a solution of commercial (−)-(2S,3S)-2,3-epoxycinnamyl alcohol (10.0 mmol) in dimethoxyethane (50 mL) is added a 3.4 M solution of sodium bis(2-methoxyethoxy)aluminum hydride (Red-A1) in toluene (10.5 mmol) dropwise under nitrogen at 0° C. After stirring at room temperature for 3 h, the solution is diluted with ether and quenched with 5% HCl solution. After further stirring at room temperature for 30 min, the white precipitate formed is removed by filtration and boiled with ethyl acetate and filtered again. The combined organic extracts are dried and concentrated to give (R)-1-phenyl-1,3-dihydroxypropane. quenched with 5% HCl solution After further stirring at room temperature for 30 min the white precipitate formed is removed by filtration filtered again The combined organic extracts are dried concentrated

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

Procedure: To a solution of (-)-(2S,3S)-epoxycinnamyl alcohol (1) (1.5 g, 10.0 mmol) (synthesized by the method disclosed in Gao et al., J. Org. Chem., Vol. 53, No. 17, pp. 4081-4084 (1988.), in dimethoxyethane (50 mL) was added a 3.4 molar solution of REd-Al in toluene (3.1 mL, 10.5 mmol) dropwise under nitrogen at 0° C. After stirring at room temperature for three hours, the solution was diluted with ether and quenched with 5% HCl solution. After stirring at room temperature for 30 min, the resulting white precipitate formed was filtered and boiled with ethyl acetate and filtered again. The combined organic solutions were dried with magnesium sulfate. Concentration gave (R)-3-phenyl-1,3-dihydroxypropane (2) as a slightly yellow oil which was used without further purification (1.5 g, 98%): 1H NMR (CDCl3) δ7.2-7.3 (m, 5H), 4.88-4.98 (m, 1H), 3.78-3.86(t, J=7.5 Hz, 2), 3.3-3.4 (br. s, 1H), 2.85-2.95 (br. s, 1H), 1.84-2.08 (m, 2H); the ratio of 1,3-diol to 1,2-diol was 20:1 by 1H NMR analysis of the derived diacetate. quenched with 5% HCl solution After stirring at room temperature for 30 min the resulting white precipitate formed was filtered filtered again The combined organic solutions were dried with magnesium sulfate Concentration

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

Procedure: To a solution of (-)-(2S,3S)-epoxycinnamyl alcohol (1) (1.5 g, 10.0 mmol) (synthesized by the method disclosed in Gao et al., J. Org. Chem., Vol. 53, No. 17, pp. 4081-4084 (1988.), in dimethoxyethane (50 mL) was added a 3.4 molar solution of REd-Al in toluene (3.1 mL, 10.5 mmol) dropwise under nitrogen at 0° C. After stirring at room temperature for three hours, the solution was diluted with ether and quenched with 5% HCl solution. After stirring at room temperature for 30 min, the resulting white precipitate formed was filtered and boiled with ethyl acetate and filtered again. The combined organic solutions were dried with magnesium sulfate. Concentration gave (R)-3-phenyl-1,3-dihydroxypropane (2) as a slightly yellow oil which was used without further purification (1.5 g, 98%): 1H NMR (CDCl3) δ7.2-7.3 (m, 5H), 4.88-4.98 (m, 1H), 3.78-3.86(t, J=7.5 Hz, 2), 3.3-3.4 (br. s, 1H), 2.85-2.95 (br. s, 1H), 1.84-2.08 (m, 2H); the ratio of 1,3-diol to 1,2-diol was 20:1 by 1H NMR analysis of the derived diacetate. quenched with 5% HCl solution After stirring at room temperature for 30 min the resulting white precipitate formed was filtered filtered again The combined organic solutions were dried with magnesium sulfate Concentration

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

Procedure: To a solution of (-)-(2S,3S)-epoxycinnamyl alcohol (1) (1.5 g, 10.0 mmol) (synthesized by the method disclosed in Gao et al., J. Org. Chem., Vol. 53, No. 17, pp. 4081-4084 (1988.), in dimethoxyethane (50 mL) was added a 3.4 molar solution of Red-Al® in toluene (3.1 mL, 10.5 mmol) dropwise under nitrogen at 0° C. After stirring at room temperature for three hours, the solution was diluted with ether and quenched with 5% HCl solution. After stirring at room temperature for 30 min, the resulting white precipitate formed was filtered and boiled with ethyl acetate and filtered again. The combined organic solutions were dried with magnesium sulfate. Concentration gave (R)-3-phenyl-1,3-dihydroxypropane (2) as a slightly yellow oil which was used without further purification (1.5 g, 98%): 1H NMR (CDCl3) δ7.2-7.3 (m, 5 H), 4.88-4.98 (m, 1 H), 3.78-3.86(t, J=7.5 Hz, 2), 3.3-3.4 (br. s, 1 H), 2.85-2.95 (br. s, 1 H) , 1.84-2.08 (m, 2 H); the ratio of 1,3-diol to 1,2-diol was 20:1 by 1H NMR analysis of the derived diacetate. quenched with 5% HCl solution After stirring at room temperature for 30 min the resulting white precipitate formed was filtered filtered again The combined organic solutions were dried with magnesium sulfate Concentration

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

Procedure: To a solution of (-)-(2S,3S)-epoxycinnamyl alcohol 1) (1.5 g, 10.0 mmol) (synthesized by the method disclosed in Gao et al., J. Org. Chem., Vol. 53, No. 17, ppg 4081-4084 (1988.), in dimethoxyethane (50 mL) was added a 3.4 molar solution of REd-Al in toluene (3.1 mL, 10.5 mmol) dropwise under nitrogen at 0° C. After stirring at room temperature for three hours, the solution was diluted with ether and quenched with 5% HCl solution. After stirring at room temperature for 30 min, the resulting white precipitate formed was filtered and boiled with ethyl acetate and filtered again. The combined organic solutions were dried with magnesium sulfate. Concentration gave (R)-3-phenyl-1,3-dihydroxypropane (2) as a slightly yellow oil which was used without further purfication (1.5 g, 98%): 1H NMR (CDCl3) &7.2-7.3 (m, 5H), 4.88-4.98 (m, 1H), 3.78-3.86(t, J= 7.5 Hz, 2), 3.3-3.4 (br. s, 1H), 2.85-2.95 (br. s, 1H), 1.84-2.08 (m, 2H); the ratio of 1,3-diol to 1,2-diol was 20:1 by 1H NMR analysis of the derived diacetate. quenched with 5% HCl solution After stirring at room temperature for 30 min the resulting white precipitate formed was filtered filtered again The combined organic solutions were dried with magnesium sulfate Concentration

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

Procedure: To a solution of commercial (−)-(2S, 3S)-2,3-epoxycinnamyl alcohol (10.0 mmol) in dimethoxyethane (50 mL) is added a 3.4 M solution of sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al) in toluene (10.5 mmol) dropwise under nitrogen at 0 C. After stirring at room temperature for 3 h, the solution is diluted with ether and quenched with 5% HCl solution. After further stirring at room temperature for 30 min, the white precipitate formed is removed by filtration and boiled with ethyl acetate and filtered again. The combined organic extracts are dried and concentrated to give (R)-1-phenyl-1,3-dihydroxypropane. quenched with 5% HCl solution After further stirring at room temperature for 30 min the white precipitate formed is removed by filtration filtered again The combined organic extracts are dried concentrated

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

Procedure: To a solution of (-)-(2S,3S)-epoxycinnamyl alcohol (1) (1.5 g, 10.0 mmol) (synthesized by the method disclosed in Gao et al., J. Org. Chem., Vol. 53, No. 17, pp. 4081-4084 (1988.), in dimethoxyethane (50 mL) was added a 3.4 molar solution of REd-Al in toluene (3.1 mL, 10.5 mmol) dropwise under nitrogen at 0° C. After stirring at room temperature for three hours, the solution was diluted with ether and quenched with 5% HCl solution. After stirring at room temperature for 30 min, the resulting white precipitate formed was filtered and boiled with ethyl acetate and filtered again. The combined organic solutions were dried with magnesium sulfate. Concentration gave (R)-3-phenyl-1,3-dihydroxypropane (2) as a slightly yellow oil which was used without further purification (1.5 g, 98%): 1H NMR (CDCl3) δ7.2-7.3 (m, 5 H), 4.88-4.98 (m, 1 H), 3.78-3.86(t, J=7.5 Hz, 2), 3.3-3.4 (br. s, 1 H), 2.85-2.95 (br. s, 1 H), 1.84-2.08 (m, 2 H); the ratio of 1,3-diol to 1,2-diol was 20:1 by 1H NMR analysis of the derived diacetate. quenched with 5% HCl solution After stirring at room temperature for 30 min the resulting white precipitate formed was filtered filtered again The combined organic solutions were dried with magnesium sulfate Concentration

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

Procedure: To a solution of commercial (−)-(2S,3S)-2,3-epoxycinnamyl alcohol (10.0 mmol) in dimethoxyethane (50 mL) is added a 3.4 M solution of sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al) in toluene (10.5 mmol) dropwise under nitrogen at 0° C. After stirring at room temperature for 3 h, the solution is diluted with ether and quenched with 5% HCl solution. After further stirring at room temperature for 30 min, the white precipitate formed is removed by filtration and boiled with ethyl acetate and filtered again. The combined organic extracts are dried with magnesium sulfate and concentrated to give (R)-3-phenyl-1,3-dihydroxypropane. quenched with 5% HCl solution After further stirring at room temperature for 30 min the white precipitate formed is removed by filtration filtered again The combined organic extracts are dried with magnesium sulfate concentrated

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

Procedure: To a solution of commercial (−)-(2S,3S)-2,3-epoxycinnamyl alcohol (10.0 mmol) in dimethoxyethane (50 mL) is added a 3.4 M solution of sodium bis(2-methoxyethoxy)aluminum hydride (Red-A1) in toluene (10.5 mmol) dropwise under nitrogen at 0° C. After stirring at room temperature for 3 h, the solution is diluted with ether and quenched with 5% HCl solution. After further stirring at room temperature for 30 min, the white precipitate formed is removed by filtration and boiled with ethyl acetate and filtered again. The combined organic extracts are dried and concentrated to give (R)-1-phenyl-1,3-dihydroxypropane. quenched with 5% HCl solution After further stirring at room temperature for 30 min the white precipitate formed is removed by filtration filtered again The combined organic extracts are dried concentrated

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

Procedure: To a solution of (-)-(2S,3S)-epoxycinnamyl alcohol (1) (1.5 g, 10.0 mmol) (synthesized by the method disclosed in Gao et al., J. Org. Chem., Vol. 53, No. 17, pp. 4081-4084 (1988.), in dimethoxyethane (50 mL) was added a 3.4 molar solution of REd-Al in toluene (3.1 mL, 10.5 mmol) dropwise under nitrogen at 0° C. After stirring at room temperature for three hours, the solution was diluted with ether and quenched with 5% HCl solution. After stirring at room temperature for 30 min, the resulting white precipitate formed was filtered and boiled with ethyl acetate and filtered again. The combined organic solutions were dried with magnesium sulfate. Concentration gave (R)-3-phenyl-1,3-dihydroxypropane (2) as a slightly yellow oil which was used without further purification (1.5 g, 98%): 1H NMR (CDCl3) δ7.2-7.3 (m, 5H), 4.88-4.98 (m, 1H), 3.78-3.86(t, J=7.5 Hz, 2), 3.3-3.4 (br. s, 1H), 2.85-2.95 (br. s, 1H), 1.84-2.08 (m, 2H); the ratio of 1,3-diol to 1,2-diol was 20:1 by 1H NMR analysis of the derived diacetate. quenched with 5% HCl solution After stirring at room temperature for 30 min the resulting white precipitate formed was filtered filtered again The combined organic solutions were dried with magnesium sulfate Concentration

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

Procedure: To a solution of commercial (−)-(2S, 3S)-2,3-epoxycinnamyl alcohol (10.0 mmol) in dimethoxyethane (50 mL) is added a 3.4 M solution of sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al) in toluene (10.5 mmol) dropwise under nitrogen at 0° C. After stirring at room temperature for 3 h, the solution is diluted with ether and quenched with 5% HCl solution. After further stirring at room temperature for 30 min, the white precipitate formed is removed by filtration and boiled with ethyl acetate and filtered again. The combined organic extracts are dried with magnesium sulfate and concentrated to give (R)-3-phenyl-1,3-dihydroxypropane. quenched with 5% HCl solution After further stirring at room temperature for 30 min the white precipitate formed is removed by filtration filtered again The combined organic extracts are dried with magnesium sulfate concentrated

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

Procedure: To a solution of commercial (−)-(2S,3S)-2,3-epoxycinnamyl alcohol (10.0 mmol) in dimethoxyethane (50 mL) is added a 3.4 M solution of sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al) in toluene (10.5 mmol) dropwise under nitrogen at 0° C. After stirring at room temperature for 3 h, the solution is diluted with ether and quenched with 5% HCl solution. After further stirring at room temperature for 30 min, the white precipitate formed is removed by filtration and boiled with ethyl acetate and filtered again. The combined organic extracts are dried with magnesium sulfate and concentrated to give (R)-3-phenyl-1,3-dihydroxypropane. quenched with 5% HCl solution After further stirring at room temperature for 30 min the white precipitate formed is removed by filtration filtered again The combined organic extracts are dried with magnesium sulfate concentrated