Reaction #52031

Reaction equation

ethyl bromoacetate

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

tetrahydrofuran

Sodium hydride

→

(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-ylmethoxy)-acetic acid ethyl ester

Solvents

ethyl acetate

Conditions

Workup

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for another hour at 25° C
3. 3
   Washwashed with 1M hydrochloric acid
4. 4
   Washwashed with a 1M aqueous solution of sodium hydrogen carbonate
5. 5
   Concentrationconcentrated

Procedure

(2,3-Dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol (6.9 g, 40 mmol) was dissolved into tetrahydrofuran (100 mL), blanketed by nitrogen. Sodium hydride (1.9 g) was added in portions after which the reaction mixture was stirred for another 30 min. Then ethyl bromoacetate (5.3 mL) was added dropwise and stirring was continued for another hour at 25° C. The reaction mixture was then poured into ethyl acetate, washed with 1M hydrochloric acid, washed with a 1M aqueous solution of sodium hydrogen carbonate and concentrated. This resulted in quantitative formation of pure (2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-ylmethoxy)-acetic acid ethyl ester as demonstrated by NMR and mass spectroscopy.

Source