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p-Toluenesulfonic acid → Ethyl 2-allyl-3-(2-ethylphenyl)-3-oxopropionate

HRID 1252782
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HRID 1252782 반응식
[CH2:1]([C:4]([C:17](=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH3:25])(C(OCC)=O)[C:5]([O:7][C:8](C)(C)[CH3:9])=[O:6])[CH:2]=[CH2:3].C(OC(=O)C)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[CH2:1]([CH:4]([C:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH3:25])=[O:26])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:2]=[CH2:3]
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참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 19809551t-Butyl ethyl 2-allyl-2-(2-ethylbenzoyl)malonate

생성물 1

HCID 13459157Ethyl 2-allyl-3-(2-ethylphenyl)-3-oxopropionate수율 71.6%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
140 °C

실험 절차

A mixture of t-butyl ethyl 2-allyl-2-(2-ethylbenzoyl)malonate (14.3 g.), acetic anhydride (4 ml.) and p-toluenesulphonic acid (100 mg.) in acetic acid (200 ml.) was heated at 140° C. under nitrogen for 75 minutes and then evaporated. The residue was shaken with a mixture of saturated sodium bicarbonate solution (100 ml.) and ethyl acetate (100 ml.). The organic phase was dried (MgSO4) and evaporated. The oil obtained (9.3 g.) was purified by flash column chromatography (280 g.) using toluene as eluant to give ethyl 2-allyl-3-(2-ethylphenyl)-3-oxopropionate (7.4 g.) as a pale yellow oil; NMR: 1.19 (6H,m), 2.74 (4H,m), 4.15 (3H,m), 5.05 (2H,m), 5.79 (1H,m), 7.30 (3H,m) and 7.61 (1H,m) ppm.

후처리

  1. customevaporated
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customThe oil obtained (9.3 g.)
  5. customwas purified by flash column chromatography (280 g.)

출처 및 근거

ORD 기록
ord-4a212d9d183144e7b1fcd4c850a9fd03
출처 데이터셋
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04745198

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