3-methoxy-4-(2-morpholin-4-ylethoxy)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:; See reaction.notes.procedure_details.

Procedure: 3-Methoxy-4-(2-morpholin-4-yl-ethoxy)-benzaldehyde was prepared from N-(2-hydroxyethyl)morpholine (Aldrich) and vanillin (Aldrich) by method H above.

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

Procedure: 3-Hydroxy-3-[3-methoxy-4-[2-(4-morpholinyl)-ethoxy]-phenyl]-1-propyne was prepared according to Method A above from 3-methoxy-4-(2-morpholin-4-yl-ethoxy)-benzaldehyde (0.60 g, 2.26 mmol) (see below) in THF (25 mL) and ethynylmagnesium chloride (5 mmol, 10 mL, 0.5M solution in tetrahydrofuran) (Aldrich). (Yield 502 mg, 76%).

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

Procedure: 3-Hydroxy-3-[3-methoxy-4-[2-(4-morpholinyl)-ethoxy]-phenyl]-1-propyne was prepared according to Method A above from 3-methoxy-4-(2-morpholin-4-yl-ethoxy)-benzaldehyde (0.60 g, 2.26 mmol) (see below) in THF (25 mL) and ethynylmagnesium chloride (5 mmol, 10 mL, 0.5M solution in tetrahydrofuran) (Aldrich). (Yield 502 mg, 76%).

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of vanilin (76.1 g) in N,N-dimethylformamide (500 mL) is added successively 4-(2-chloroethyl)morpholine hydrochloride (130 g), sodium iodide (7.5 g), and potassium carbonate (207 g). The mixture is stirred at 80° C. for 15 hours. The reaction mixture is concentrated in vacuo. The residue is diluted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. To the residue is added diisopropyl ether and the resultant crystals are collected by filtration to give 3-methoxy-4-(2-morpholinoethoxy)-benzaldehyde (112.6 g, yield; 85%) as orange crystals. MS (APCI) m/z: 266 [M+H]+ The reaction mixture is concentrated in vacuo The residue is diluted with ethyl acetate washed with saturated brine dried over anhydrous sodium sulfate concentrated in vacuo To the residue is added diisopropyl ether the resultant crystals are collected by filtration

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of vanilin (76.1 g) in N,N-dimethylformamide (500 mL) is added successively 4-(2-chloroethyl)morpholine hydrochloride (130 g), sodium iodide (7.5 g), and potassium carbonate (207 g). The mixture is stirred at 80° C. for 15 hours. The reaction mixture is concentrated in vacuo. The residue is diluted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. To the residue is added diisopropyl ether and the resultant crystals are collected by filtration to give 3-methoxy-4-(2-morpholinoethoxy)-benzaldehyde (112.6 g, yield; 85%) as orange crystals. MS (APCI) m/z: 266 [M+H]+ The reaction mixture is concentrated in vacuo The residue is diluted with ethyl acetate washed with saturated brine dried over anhydrous sodium sulfate concentrated in vacuo To the residue is added diisopropyl ether the resultant crystals are collected by filtration

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

Procedure: 3-Methoxy-4-(2-morpholin-4-yl-ethoxy)-benzaldehyde was prepared from N-(2-hydroxyethyl)morpholine (Aldrich) and vanillin (Aldrich) by method H above.

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

Procedure: 3-Hydroxy-3-[3-methoxy-4-[2-(4-morpholinyl)-ethoxy]-phenyl]-1-propyne was prepared according to Method A above from 3-methoxy-4-(2-morpholin-4-yl-ethoxy)-benzaldehyde (0.60 g, 2.26 mmol) (see below) in THF (25 mL) and ethynylmagnesium chloride (5 mmol, 10 mL, 0.5M solution in tetrahydrofuran) (Aldrich). (Yield 502 mg, 76%).

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of vanilin (76.1 g) in N,N-dimethylformamide (500 mL) is added successively 4-(2-chloroethyl)morpholine hydrochloride (130 g), sodium iodide (7.5 g), and potassium carbonate (207 g). The mixture is stirred at 80° C. for 15 hours. The reaction mixture is concentrated in vacuo. The residue is diluted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. To the residue is added diisopropyl ether and the resultant crystals are collected by filtration to give 3-methoxy-4-(2-morpholinoethoxy)-benzaldehyde (112.6 g, yield; 85%) as orange crystals. MS (APCI) m/z: 266 [M+H]+ The reaction mixture is concentrated in vacuo The residue is diluted with ethyl acetate washed with saturated brine dried over anhydrous sodium sulfate concentrated in vacuo To the residue is added diisopropyl ether the resultant crystals are collected by filtration