Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → (E)-methyl 3-[3-(methylcarbamoyl)phenyl]prop-2-enoate

HRID 16912

반응식

HRID 16912 반응식
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([NH:8][CH3:9])=[O:7])=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:20][C:21]([O:23][CH3:24])=[O:22])C=CC=CC=1>ClCCl>[CH3:9][NH:8][C:6]([C:5]1[CH:4]=[C:3](/[CH:1]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])[CH:12]=[CH:11][CH:10]=1)=[O:7]

참가 물질

4

반응물 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 220514333-formyl-N-methylbenzamide

생성물 1

HCID 66589796(E)-methyl 3-[3-(methylcarbamoyl)phenyl]prop-2-enoate수율 97%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 3-formyl-N-methylbenzamide (2.9 g, 17.77 mmol) and methyl 2-triphenylphosphoranylideneacetate (8.91 g, 26.66 mmol) in dichloromethane (85 mL), was stirred at room temperature for 18 h. The reaction mixture was evaporated to dryness. The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford impure product. Re-purified by silica column chromatography, eluting with a gradient of 50 to 100% EtOAc in hexanes. Pure fractions were evaporated to dryness to afford (E)-methyl 3-[3-(methylcarbamoyl)phenyl]prop-2-enoate (3.77 g, 97%).

후처리

  1. customThe reaction mixture was evaporated to dryness
  2. customThe crude product was purified by silica column chromatography
  3. washeluting with a gradient of 0 to 10% MeOH in DCM
  4. customPure fractions were evaporated to dryness
  5. customto afford impure product
  6. washRe-purified by silica column chromatography, eluting with a gradient of 50 to 100% EtOAc in hexanes
  7. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-24af0df68b554f1aa00326ca1f29ca6d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737149B2

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