1-(2-chloroethoxy)propane

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:

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 4-hydroxybenzoic acid (3.04 g) and anhydrous potassium carbonate (5.52 g) in N,N-dimethylformamide (20 ml) was added 2-propyloxyethyl chloride (2.94 g), and the mixture was stirred at room temperature overnight, and then stirred at 80° C. for 8 hours. To a reaction solution was added water, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, successively, dried and concentrated under reduced pressure to give the title compound (5.21 g; crude). stirred at 80° C. for 8 hours the mixture was extracted with ethyl acetate The organic layer was washed with water a saturated aqueous solution of sodium chloride, successively, dried concentrated under reduced pressure

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

Procedure: 1.7 g (12.48 mmol) of potassium carbonate were added at 60° C. to a suspension of 2.2 g (7.8 mmol) of 7-benzyl-3-propylxanthine (prepared according to Example 4a) in 70 ml of dimethylformamide and the mixture was stirred at this temperature for one hour. 1.3 ml (10.14 mmol) of 2-propoxyethyl chloride were then added dropwise and the mixture was stirred at 80° C. for 10 hours. 1.2 ml of methanol and 14 ml of water were then added, and the mixture was allowed to stand overnight, treated with a further 70 ml of water and extracted three times using 84 ml of methyl tert-butyl ether each time. The combined organic phases were washed twice with 42 ml of water each time, dried using magnesium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column, dichloromethae/methanol (19/0.1). the mixture was stirred at 80° C. for 10 hours to stand overnight extracted three times The combined organic phases were washed twice with 42 ml of water each time dried concentrated under reduced pressure The crude product was purified by flash chromatography on a silica gel column, dichloromethae/methanol (19/0.1)

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