Ethyl bromoacetate → Ethyl 2-thienyloxyacetate

To a solution of 2-hydroxy-thiophene (32 g, 320 mmol) in CHCl3 (500 mL) is added ethyl bromoacetate (53.4 g, 320 mmol). To the resulting solution is added a solution containing n-Bu4NHSO4 (25 g, 74 mmol) and NaOH (15.8 g, 394 mmol) in water (500 mL). After addition, the solution is stirred vigorously using mechanical stirring. The reaction is stirred for 12 hours. After this time, the layers are separated. The aqueous layer is extracted with CHCl3. The combined organic layers are washed with water and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated under vacuum. The resulting crude product is purified by column chromatography eluting with a gradient of 30%CH2Cl2:hexanes to 60%CH2Cl2:hexanes. The title compound (11.5 g, 62 mmol) is obtained as 1H NMR (CDCl3, 300 MHz) δ6.68 (dd, 1H), 6.60 (d, 1H), 6.22 (d, 1H), 4.62 (s, 2H), 4.30 (q, 2H), 1.31 (t, 3H).

1. additionTo the resulting solution is added a solution
2. additionAfter addition
3. stirringThe reaction is stirred for 12 hours
4. customAfter this time, the layers are separated
5. extractionThe aqueous layer is extracted with CHCl3
6. washThe combined organic layers are washed with water and saturated NaCl
7. dry with materialThe organic layer is dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated under vacuum
10. customThe resulting crude product is purified by column chromatography
11. washeluting with a gradient of 30%CH2Cl2

ORD record

ord-c655edf4b0934b1986692f79e66d8f2b

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612075B2