Toluene → Ethyl 2-(4-methoxybenzoyl)-4-nitromethyl-3-(1,3-benzodioxole-5-yl)butyrate

HRID 2999

반응식

HRID 2999 반응식
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[CH3:2].[N+:17]([CH:20]=[CH:21][C:22]1[CH:30]=[CH:29][C:25]2OCOC=2C=1)([O-:19])=[O:18].[C:31]([O:34][CH2:35][CH3:36])(=[O:33])C.[C:37]1(C)C=CC=CC=1>C(Cl)Cl.N12CCCN=C1CCCCC2>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]([CH:5]([CH:22]([C:30]2[CH:29]=[CH:25][C:36]3[O:33][CH2:31][O:34][C:35]=3[CH:37]=2)[CH2:21][CH2:20][N+:17]([O-:19])=[O:18])[C:4]([O:3][CH2:1][CH3:2])=[O:16])=[O:15])=[CH:12][CH:11]=1

참가 물질

7

반응물 4

HCID 1140Toluene2회HCID 8857Ethyl AcetateHCID 76150Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl esterHCID 949455-(2-Nitroethenyl)-1,3-benzodioxole

생성물 1

HCID 22322609Ethyl 2-(4-methoxybenzoyl)-4-nitromethyl-3-(1,3-benzodioxole-5-yl)butyrate

시약·촉매·용매 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene촉매2회HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

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.

후처리

  1. dissolutiondissolved
  2. stirringThe solution was stirred
  3. temperaturewithout heating for 30 minutes
  4. stirringAfter stirring an additional 45 minutes
  5. washthe organic phase was washed with dilute hydrochloric acid and NaCl solution
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue obtained
  9. customwas chromatographed on silica gel eluting with 3:1 hexane-ethyl acetate

출처 및 근거

ORD 기록
ord-5e03f22df256414685d3dd552140fa88
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731434

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