반응 #47990

반응 방정식

Methyl 4-hydroxy-3-methoxybenzoate

tert-butyl 2-bromopropanoate

cesium carbonate

→

2-(2-methoxy-4-(methoxycarbonyl)phenoxy)propanoic acid

용매

DMF

반응 조건

후처리

1. 1
   기타vial equipped with a stir bar
2. 2
   기타sealed
3. 3
   기타The solvent was removed
4. 4
   workup.DISSOLUTIONthe remained sticky oil was dissolved in DCM (7 mL)
5. 5
   기타was separated from the mixture
6. 6
   세척The aqueous layer was washed with DCM (2×10 mL)
7. 7
   추출Aqueous was extracted with DCM
8. 8
   건조with ethyl acetate, dried with sodium sulfate
9. 9
   농축concentrated to an oil
10. 10
    workup.DISSOLUTIONThe crude product was dissolved in DCM (4 mL)
11. 11
    기타a pure product (0.530 g) precipitate out from the solution
12. 12
    workup.ADDITIONby adding diethyl ether (4 mL)

실험 절차

Methyl 4-hydroxy-3-methoxybenzoate (1.09 g, 5.98 mmol) and tert-butyl 2-bromopropanoate (1.25 g, 0.97 mL, 5.98 mmol) and cesium carbonate (1.95 g, 5.98 mmol) were added into DMF (10 mL) in a 20 mL microwave vial equipped with a stir bar and sealed. The mixture was heated in Biotage microwave synthesizer for 1 hour at 100° C. The solvent was removed and the remained sticky oil was dissolved in DCM (7 mL) and TFA (7 mL). The mixture was stirred overnight. The reaction mixture was neutralized with sodium bicarbonate and organic layer was separated from the mixture. The aqueous layer was washed with DCM (2×10 mL), combined organics and acidified to around pH5 with 2N HCl. Aqueous was extracted with DCM and then with ethyl acetate, dried with sodium sulfate and concentrated to an oil. The crude product was dissolved in DCM (4 mL) and a pure product (0.530 g) precipitate out from the solution by adding diethyl ether (4 mL).

출처