반응 #3095

반응 방정식

ethyl(4-methoxybenzoyl)acetate

ethyl acetate

Toluene

5-(2-nitrovinyl)-1,3-benzodioxole

toluene

→

desired product

Ethyl 2-(4-methoxybenzoyl)-4-nitromethyl-3-(1.3-benzodioxole-5-yl)butyrate

용매

methylene chloride

반응 조건

후처리

1. 1
   workup.DISSOLUTIONdissolved
2. 2
   workup.STIRRINGThe solution was stirred
3. 3
   온도without heating for 30 minutes
4. 4
   workup.STIRRINGAfter stirring an additional 45 minutes
5. 5
   세척the organic phase was washed with dilute hydrochloric acid and NaCl solution
6. 6
   건조The organic phase was dried over sodium sulfate
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The residue obtained
9. 9
   기타was chromatographed on silica gel eluting with 3:1 hexane-ethyl acetate

실험 절차

To ethyl(4-methoxybenzoyl)acetate (23.0 g, 0.104 mol), prepared by the method of Krapcho et al., Org. Syn. 47, 20 (1967), and 5-(2-nitrovinyl)-1,3-benzodioxole (17.0 g, 0.088 mol) dissolved in 180 mL of toluene and heated to 80° C. was added 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU, 0.65 g) with stirring. The mixture was heated until all the nitro starting material dissolved. The solution was stirred without heating for 30 minutes and then an additional 0.65 g of DBU was added. After stirring an additional 45 minutes, thin layer chromatography (5% ethyl acetate in methylene chloride) indicated the absence of nitro starting material. Toluene (200 mL) was added, and the organic phase was washed with dilute hydrochloric acid and NaCl solution. The organic phase was dried over sodium sulfate and then concentrated under reduced pressure. The residue obtained was chromatographed on silica gel eluting with 3:1 hexane-ethyl acetate to give 21.22 g of the desired product as a mixture of isomers and 9.98 g. of recovered ethyl(4-methoxybenzoyl)acetate.

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