반응 #328054

반응 방정식

cyclohexane-1,2-dione

methyl 2-(2-oxopropylthio)acetate

sodium

→

methyl 3-acetyl-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate

수율 27.6%

용매

MeOH

MeOH

반응 조건

후처리

1. 1
   workup.WAITat 50-60° C. for additional 1.5 hour
2. 2
   기타Remove the solvent under vacuum
3. 3
   workup.ADDITIONdilute the residue with water (100 mL)
4. 4
   추출Extract the aqueous mixture with ethyl acetate (100 mL×3)
5. 5
   세척The combined organic layers are washed with brine
6. 6
   건조dried over anhydrous Na2SO4
7. 7
   기타evaporated under vacuum
8. 8
   기타Purify the residue by a flash column on silica gel eluting with PE

실험 절차

Add methyl 2-(2-oxopropylthio)acetate (35.4 g, 183.2 mmol) to a freshly prepared solution of solid sodium (8.78 g, 381.5 mmol) in dry MeOH (300 mL) at 0° C., followed by addition of a solution of cyclohexane-1,2-dione (20 g, 152.6 mmol) in MeOH (30 mL). Stir the mixture at 0° C. for 30 min and then at 50-60° C. for additional 1.5 hour. Remove the solvent under vacuum and dilute the residue with water (100 mL). Extract the aqueous mixture with ethyl acetate (100 mL×3). The combined organic layers are washed with brine, dried over anhydrous Na2SO4, and evaporated under vacuum. Purify the residue by a flash column on silica gel eluting with PE:EtOAc (50:1 to 30:1) to afford methyl 3-acetyl-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate as a white solid (10 g, 27.6%). MS (m/z): 239 (M+1).

출처