2,3-dihydro-1,4-benzodioxin-3-ylmethanol

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: A mixture of thionyl chloride (36.0 g, 0.3 mol) and 2-hydroxymethyl-1,4-benzodioxan (25.0 g, 0.15 mol) was stirred and heated under reflux for 0.75 h. The reaction mixture was concentrated under reduced pressure, and the residue was distilled, to afford 2-chloromethyl-1,4-benzodioxan, b.p. 140°-146°/22 mm Hg. heated under reflux for 0.75 h The reaction mixture was concentrated under reduced pressure the residue was distilled

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

Procedure: In a similar manner to Example (1a), with benzyl alcohol replaced by (1,4-benzodioxan-2-yl)methanol, 1-[(1,4-benzodioxan-2-yl)methoxy]-2,3-epoxypropane is obtained. The latter derivative, when condensed according to Example (1b) with 2-aminoethyl hydrogen sulfate, leads to the derivative of formula: ##STR26## Empirical formula: C18H23NO8Molecular mass: 381.38

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

Procedure: Triethylamine (4.2 ml, 30 mmol was added, in one portion, and then, in portions, para-toluenesulfonyl chloride (5.7 g, 30 mmol was added, to a solution of 2-hydroxymethyl-1,4-benzodioxane (Maybridge, 5 g, 30 mmol) in methylene chloride (50 ml). A mild exothermic reaction ensued. The reaction mixture was stirred overnight. Precipitated triethylamine hydrochloride was separated by filtration and washed with methylene chloride (50 ml). The organic medium was washed with 10% aqueous hydrochloric acid (50 ml , water 50 ml , brine (30 ml), and dried over sodium sulfate. Purification of the crude product by column chromatography (400 g fine silica, hexane-ethyl acetatetriethylamine; 100:100:1) yielded pure (1,4-benzodioxan-2-yl)methyl tosylate (66%). A mild exothermic reaction Precipitated triethylamine hydrochloride was separated by filtration washed with methylene chloride (50 ml) The organic medium was washed with 10% aqueous hydrochloric acid (50 ml , water 50 ml , brine (30 ml) dried over sodium sulfate Purification of the crude product by column chromatography (400 g fine silica, hexane-ethyl acetatetriethylamine; 100:100:1)

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

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