3-phenylbutane-1,3-diol

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

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

Procedure: To a solution of 3-phenylbutane-1,3-diol (68 g, 0.41 mol) in dry CH2Cl2 (500 mL) was added dropwise a solution of TsCl (78 g, 0.41 mol) and triethylamine (71 mL, 0.45 mol) in dry CH2Cl2 (500 mL) at 0° C. The mixture was stirred overnight. The mixture was poured into water and separated. The aqueous layer was extracted with CH2Cl2 (200 mL) twice. The organic layer was combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give the crude product. The crude product was purified by column chromatography to give 3-hydroxy-3-phenylbutyl 4-methylbenzenesulfonate (62 g, 42%). 1H NMR (400 MHz, CDCl3): δ=1.55 (s, 3H), 1.93 (w, 1H), 2.19˜2.24 (q, 2H), 2.45 (s, 3H), 3.87˜4.01 (m, 1H), 4.09˜4.16 (m, 1H), 7.19˜7.34 (m, 7H), 7.68˜7.76 (d, 2H). separated The aqueous layer was extracted with CH2Cl2 (200 mL) twice washed with brine dried over anhydrous Na2SO4 concentrated to give the crude product The crude product was purified by column chromatography

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

Procedure: A solution of 2-phenylpent-4-en-2-ol (74 g, 0.457 mol) in dry CH2Cl2 (1 L) was treated with ozone at −78° C. until the mixture turned blue. The system was then flushed with oxygen to remove excess ozone. NaBH4 (42.8 g, 1.143 mol) was added to the mixture in portions at −20° C. The mixture was stirred overnight at rt. The mixture was quenched with water and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give 3-phenylbutane-1,3-diol (67.8 g), which was used for the next step without purification. The system was then flushed with oxygen to remove excess ozone The mixture was quenched with water the layers were separated The aqueous layer was extracted with CH2Cl2 (2×) washed with brine dried over anhydrous Na2SO4 concentrated

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

Procedure: A solution of 2-phenylpent-4-en-2-ol (74 g, 0.457 mol) in dry CH2Cl2 (1 L) was treated with ozone at −78° C. until the mixture turned blue. The system was then flushed with oxygen to remove excess ozone. NaBH4 (42.8 g, 1.143 mol) was added to the mixture in portions at −20° C. The mixture was stirred overnight at rt. The mixture was quenched with water and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give 3-phenylbutane-1,3-diol (67.8 g), which was used for the next step without purification. The system was then flushed with oxygen to remove excess ozone The mixture was quenched with water the layers were separated The aqueous layer was extracted with CH2Cl2 (2×) washed with brine dried over anhydrous Na2SO4 concentrated

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

Procedure: To a solution of 3-phenylbutane-1,3-diol (68 g, 0.41 mol) in dry CH2Cl2 (500 mL) was added dropwise a solution of TsCl (78 g, 0.41 mol) and triethylamine (71 mL, 0.45 mol) in dry CH2Cl2 (500 mL) at 0° C. The mixture was stirred overnight. The mixture was poured into water and separated. The aqueous layer was extracted with CH2Cl2 (200 mL) twice. The organic layer was combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give the crude product. The crude product was purified by column chromatography to give 3-hydroxy-3-phenylbutyl 4-methylbenzenesulfonate (62 g, 42%). 1H NMR (400 MHz, CDCl3): δ=1.55 (s, 3H), 1.93 (w, 1H), 2.19˜2.24 (q, 2H), 2.45 (s, 3H), 3.87˜4.01 (m, 1H), 4.09˜4.16 (m, 1H), 7.19˜7.34 (m, 7H), 7.68˜7.76 (d, 2H). separated The aqueous layer was extracted with CH2Cl2 (200 mL) twice washed with brine dried over anhydrous Na2SO4 concentrated to give the crude product The crude product was purified by column chromatography

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

Procedure: A solution of 2-phenylpent-4-en-2-ol (74 g, 0.457 mol) in dry CH2Cl2 (1 L) was treated with ozone at −78° C. until the mixture turned blue. The system was then flushed with oxygen to remove excess ozone. NaBH4(42.8 g, 1.143 mol) was added to the mixture in portions at −20° C. The mixture was stirred overnight at rt. The mixture was quenched with water and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give 3-phenylbutane-1,3-diol (67.8 g), which was used for the next step without purification. The system was then flushed with oxygen to remove excess ozone The mixture was quenched with water the layers were separated The aqueous layer was extracted with CH2Cl2 (2×) washed with brine dried over anhydrous Na2SO4 concentrated

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

Procedure: To a solution of 3-phenylbutane-1,3-diol (68 g, 0.41 mol) in dry CH2Cl2 (500 mL) was added dropwise a solution of TsCl (78 g, 0.41 mol) and triethylamine (71 mL, 0.45 mol) in dry CH2Cl2 (500 mL) at 0° C. The mixture was stirred overnight. The mixture was poured into water and separated. The aqueous layer was extracted with CH2Cl2 (200 mL) twice. The organic layer was combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give the crude product. The crude product was purified by column chromatography to give 3-hydroxy-3-phenylbutyl 4-methylbenzenesulfonate (62 g, 42%). 1H NMR (400 MHz, CDCl3): δ=1.55 (s, 3H), 1.93 (w, 1H), 2.19˜2.24 (q, 2H), 2.45 (s, 3H), 3.87˜4.01 (m, 1H), 4.09˜4.16 (m, 1H), 7.19˜7.34 (m, 7H), 7.68˜7.76 (d, 2H). separated The aqueous layer was extracted with CH2Cl2 (200 mL) twice washed with brine dried over anhydrous Na2SO4 concentrated to give the crude product The crude product was purified by column chromatography

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

Procedure: A solution of 2-phenylpent-4-en-2-ol (74 g, 0.457 mol) in dry CH2Cl2 (1 L) was treated with ozone at −78° C. until the mixture turned blue. The system was then flushed with oxygen to remove excess ozone. NaBH4 (42.8 g, 1.143 mol) was added to the mixture in portions at −20° C. The mixture was stirred overnight at rt. The mixture was quenched with water and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give 3-phenylbutane-1,3-diol (67.8 g), which was used for the next step without purification. The system was then flushed with oxygen to remove excess ozone The mixture was quenched with water the layers were separated The aqueous layer was extracted with CH2Cl2 (2×) washed with brine dried over anhydrous Na2SO4 concentrated

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

Procedure: To a solution of 3-phenylbutane-1,3-diol (68 g, 0.41 mol) in dry CH2Cl2 (500 mL) was added dropwise a solution of TsCl (78 g, 0.41 mol) and triethylamine (71 mL, 0.45 mol) in dry CH2Cl2 (500 mL) at 0° C. The mixture was stirred overnight. The mixture was poured into water and separated. The aqueous layer was extracted with CH2Cl2 (200 mL) twice. The organic layer was combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give the crude product. The crude product was purified by column chromatography to give 3-hydroxy-3-phenylbutyl 4-methylbenzenesulfonate (62 g, 42%). 1H NMR (400 MHz, CDCl3): δ=1.55 (s, 3H), 1.93 (w, 1H), 2.19˜2.24 (q, 2H), 2.45 (s, 3H), 3.87˜4.01 (m, 1H), 4.09˜4.16 (m, 1H), 7.19˜7.34 (m, 7H), 7.68˜7.76 (d, 2H). separated The aqueous layer was extracted with CH2Cl2 (200 mL) twice washed with brine dried over anhydrous Na2SO4 concentrated to give the crude product The crude product was purified by column chromatography

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

Procedure: A solution of 2-phenylpent-4-en-2-ol (74 g, 0.457 mol) in dry CH2Cl2 (1 L) was treated with ozone at −78° C. until the mixture turned blue. The system was then flushed with oxygen to remove excess ozone. NaBH4 (42.8 g, 1.143 mol) was added to the mixture in portions at −20° C. The mixture was stirred overnight at rt. The mixture was quenched with water and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give 3-phenylbutane-1,3-diol (67.8 g), which was used for the next step without purification. The system was then flushed with oxygen to remove excess ozone The mixture was quenched with water the layers were separated The aqueous layer was extracted with CH2Cl2 (2×) washed with brine dried over anhydrous Na2SO4 concentrated