反応 #52031

反応方程式

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

溶媒

ethyl acetate

反応条件

後処理

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

実験手順

(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.

出典