Reaction #52030

Reaction equation

2-Hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid

ethyl acetate

→

(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol

Solvents

N,N-dimethylacetamide

Conditions

Workup

1. 1
   Temperatureafter which it was cooled to 25° C
2. 2
   Otherthe catalyst removed by filtration
3. 3
   Washthe filtrate washed with acidic water
4. 4
   OtherThe solvent was then removed after which pure (2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol
5. 5
   Otherwas isolated by vacuum distillation (115-120° C.; 0.05 mm Hg)

Procedure

2-Hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid (48 g, 0.184 mol) was dissolved in N,N-dimethylacetamide (500 mL), and Cu2Cr2O7 (8.6 g) and quinoline (15 drops) were added. This mixture was subsequently stirred for 2 hours at 150° C., after which it was cooled to 25° C. It was then poured into ethyl acetate, the catalyst removed by filtration and the filtrate washed with acidic water and a saturated aqueous solution of sodium chloride. The solvent was then removed after which pure (2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol was isolated by vacuum distillation (115-120° C.; 0.05 mm Hg).

Source