4-methoxy-3-(3-methoxypropoxy)benzaldehyde

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:

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

Procedure: To a solution of the title A compound, 4-methoxy-3-(3-methoxy-propoxy)-benzaldehyde (2.02 g, 8.9 mmol) in 60 mL of THF is added portion wise sodium borohydride (0.74 g, 18.73 mmol) at 0° C. The reaction mixture is stirred for 6 hours at room temperature. After addition of H2O, the aqueous layer is extracted twice with ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound as a colorless oil: TLC, Rf (hexane/AcOEt 1/1)=0.34. the aqueous layer is extracted twice with ethyl acetate The combined organic extracts are dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: To a solution of 3-hydroxy-4-methoxy-benzaldehyde (3.04 g, 20 mmol) and 3-methoxy-propanol (1.80 g, 20 mmol) in THF (150 mL) is added triphenylphosphine (5.24 g, 20 mmol) at room temperature under nitrogen atmosphere. To the stirring mixture is added diethyl azodicarboxylate (3.11 mL, 20 mmol) over 10 min at room temperature, and the resulting solution is further stirred over 20 h. THF is removed under reduced pressure and the remaining residue is purified by flash chromatography on silica gel (hexane/EtOAc 2/1) to afford the title compound: TLC, Rf (hexane/EtOAc 2/1)=0.2. THF is removed under reduced pressure the remaining residue is purified by flash chromatography on silica gel (hexane/EtOAc 2/1)

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

Procedure: To a solution of 3-hydroxy-4-methoxy-benzaldehyde (3.04 g, 20 mmol) and 3-methoxy-propanol (1.80 g, 20 mmol) in THF (150 mL) is added triphenylphosphine (5.24 g, 20 mmol) at room temperature under nitrogen atmosphere. To the stirring mixture is added diethyl azodicarboxylate (3.11 mL, 20 mmol) over 10 min at room temperature, and the resulting solution is further stirred over 20 h. THF is removed under reduced pressure and the remaining residue is purified by flash chromatography on silica gel (hexane/EtOAc 2/1) to afford the title compound: TLC, Rf (hexane/EtOAc 2/1)=0.2. THF is removed under reduced pressure the remaining residue is purified by flash chromatography on silica gel (hexane/EtOAc 2/1)

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

Procedure: To a solution of 3-hydroxy-4-methoxy-benzaldehyde (3.04 g, 20 mmol) and 3-methoxy-propanol (1.80 g, 20 mmol) in THF (150 mL) is added triphenylphosphine (5.24 g, 20 mmol) at room temperature under nitrogen atmosphere. To the stirring mixture is added diethyl azodicarboxylate (3.11 mL, 20 mmol) over 10 min at room temperature, and the resulting solution is further stirred over 20 h. THF is removed under reduced pressure and the remaining residue is purified by flash chromatography on silica gel (hexane/EtOAc 2/1) to afford the title compound: TLC, Rf (hexane/EtOAc 2/1)=0.2. THF is removed under reduced pressure the remaining residue is purified by flash chromatography on silica gel (hexane/EtOAc 2/1)

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

Procedure: Sodium borohydride (39.7 g) is added in portions to a solution of 4-methoxy-3-(3-methoxypropoxy)-benzaldehyde (336 g) in methanol (3.36 liters), the reaction temperature being maintained at 0°-5° C. When the addition is complete, the batch is stirred for a further 60 minutes at room temperature and concentrated under reduced pressure, and the residue is partitioned between ice-cooled 2N hydrochloric acid and ethyl acetate (3×2 liters). The combined organic phases are washed with water and saturated sodium hydrogen carbonate solution, added over magnesium sulfate and concentrated. Purification of the residue by FC on silica gel (dichloromethane/methanol 96:4) yields the title compound in the form of an oil (326 g): Rf (ethyl acetate/hexane 2:1)=0.31. Anal. C12H18O4 (226.27): calc. C, 63.70; H, 8.02; found C, 63.70; H, 8.24. the reaction temperature being maintained at 0°-5° C When the addition concentrated under reduced pressure the residue is partitioned between ice- cooled 2N hydrochloric acid and ethyl acetate (3×2 liters) The combined organic phases are washed with water and saturated sodium hydrogen carbonate solution added over magnesium sulfate concentrated Purification of the residue by FC on silica gel (dichloromethane/methanol 96:4)

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

Procedure: Sodium borohydride (39.7 g) is added in portions to a solution of 4-methoxy-3-(3-methoxypropoxy)-benzaldehyde (336 g) in methanol (3.36 liters), the reaction temperature being maintained at 0°-5° C. When the addition is complete, the batch is stirred for a further 60 minutes at room temperature and concentrated under reduced pressure, and the residue is partitioned between ice-cooled 2N hydrochloric acid and ethyl acetate (3×2 liters). The combined organic phases are washed with water and saturated sodium hydrogen carbonate solution, added over magnesium sulfate and concentrated. Purification of the residue by FC on silica gel (dichloromethane/methanol 96:4) yields the title compound in the form of an oil (326 g): Rf (ethyl acetate/hexane 2:1)=0.31. Anal. C12H18O4 (226.27): calc. C, 63.70; H, 8.02; found C, 63.70; H, 8.24. the reaction temperature being maintained at 0°-5° C When the addition concentrated under reduced pressure the residue is partitioned between ice- cooled 2N hydrochloric acid and ethyl acetate (3×2 liters) The combined organic phases are washed with water and saturated sodium hydrogen carbonate solution added over magnesium sulfate concentrated Purification of the residue by FC on silica gel (dichloromethane/methanol 96:4)