3-(furan-2-yl)propan-1-ol

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

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

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

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: The product from Example 50A (2.0 g, 15.9 mmol) in CH2Cl2 (50 mL) was treated with Dess-Martin periodinane (8.1 g, 19.2 mmol) in portions. The mixture was stirred at rt for 2 hrs, quenched with saturated NaS2O3, and the mixture was extracted with CH2Cl2. The CH2Cl2 layer was washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated. The resulting residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 1.44 g (73%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 2.80 (t, J=8.24, 6.41 Hz, 2H) 2.98 (t, J=7.32 Hz, 2H) 6.02 (d, J=3.97 Hz, 1H) 6.19-6.36 (m, 1H) 7.28-7.33 (m, 1H) 9.82 (s, 1H). quenched with saturated NaS2O3 the mixture was extracted with CH2Cl2 The CH2Cl2 layer was washed with saturated NaHCO3 dried over MgSO4 filtered concentrated The resulting residue was purified by column chromatography

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

Procedure: The product from Example 50A (2.0 g, 15.9 mmol) in CH2Cl2 (50 mL) was treated with Dess-Martin periodinane (8.1 g, 19.2 mmol) in portions. The mixture was stirred at rt for 2 hrs, quenched with saturated NaS2O3, and the mixture was extracted with CH2Cl2. The CH2Cl2 layer was washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated. The resulting residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 1.44 g (73%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 2.80 (t, J=8.24, 6.41 Hz, 2H) 2.98 (t, J=7.32 Hz, 2H) 6.02 (d, J=3.97 Hz, 1H) 6.19-6.36 (m, 1H) 7.28-7.33 (m, 1H) 9.82 (s, 1H). quenched with saturated NaS2O3 the mixture was extracted with CH2Cl2 The CH2Cl2 layer was washed with saturated NaHCO3 dried over MgSO4 filtered concentrated The resulting residue was purified by column chromatography

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

Procedure: To 3-(furan-2-yl)propanoic acid (1.4 g, 10 mmol) in THF (50 mL) was added dropwise borane (1M) (20 mL, 20 mmol). The mixture was stirred at rt for 12 hrs, quenched with MeOH, and the mixture was concentrated. The resulting residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 1.0 g (79%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.87-1.94 (m, 2H) 2.74 (t, J=7.32 Hz, 2H) 3.69 (t, J=6.10 Hz, 2H) 6.28 (dd, J=3.05, 1.83 Hz, 1H) 7.30 (d, J=0.92 Hz, 1H). quenched with MeOH the mixture was concentrated The resulting residue was purified by column chromatography

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

Procedure: To 3-(furan-2-yl)propanoic acid (1.4 g, 10 mmol) in THF (50 mL) was added dropwise borane (1M) (20 mL, 20 mmol). The mixture was stirred at rt for 12 hrs, quenched with MeOH, and the mixture was concentrated. The resulting residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 1.0 g (79%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.87-1.94 (m, 2H) 2.74 (t, J=7.32 Hz, 2H) 3.69 (t, J=6.10 Hz, 2H) 6.28 (dd, J=3.05, 1.83 Hz, 1H) 7.30 (d, J=0.92 Hz, 1H). quenched with MeOH the mixture was concentrated The resulting residue was purified by column chromatography

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

Procedure: The product from Example 50A (2.0 g, 15.9 mmol) in CH2Cl2 (50 mL) was treated with Dess-Martin periodinane (8.1 g, 19.2 mmol) in portions. The mixture was stirred at rt for 2 hrs, quenched with saturated NaS2O3, and the mixture was extracted with CH2Cl2. The CH2Cl2 layer was washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated. The resulting residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 1.44 g (73%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 2.80 (t, J=8.24, 6.41 Hz, 2H) 2.98 (t, J=7.32 Hz, 2H) 6.02 (d, J=3.97 Hz, 1H) 6.19-6.36 (m, 1H) 7.28-7.33 (m, 1H) 9.82 (s, 1H). quenched with saturated NaS2O3 the mixture was extracted with CH2Cl2 The CH2Cl2 layer was washed with saturated NaHCO3 dried over MgSO4 filtered concentrated The resulting residue was purified by column chromatography

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

Procedure: To 3-(furan-2-yl)propanoic acid (1.4 g, 10 mmol) in THF (50 mL) was added dropwise borane (1M) (20 mL, 20 mmol). The mixture was stirred at rt for 12 hrs, quenched with MeOH, and the mixture was concentrated. The resulting residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 1.0 g (79%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.87-1.94 (m, 2H) 2.74 (t, J=7.32 Hz, 2H) 3.69 (t, J=6.10 Hz, 2H) 6.28 (dd, J=3.05, 1.83 Hz, 1H) 7.30 (d, J=0.92 Hz, 1H). quenched with MeOH the mixture was concentrated The resulting residue was purified by column chromatography

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