Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 3-(5-methylthiophen-2-yl)prop-2-enoate

HRID 651634노트

반응식

HRID 651634 반응식
[CH3:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]([CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:12]>C(Cl)Cl>[CH3:9][O:10][C:11](=[O:12])[CH:13]=[CH:7][C:5]1[S:6][C:2]([CH3:1])=[CH:3][CH:4]=1

참가 물질

4

반응물 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 616635-Methyl-2-thiophenecarboxaldehyde

생성물 1

HCID 53641428Methyl 3-(5-methylthiophen-2-yl)prop-2-enoate수율 62.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 5-methyl-thiophene-2-carboxaldehyde (5 g, 40 mmol) in CH2Cl2 (100 mL) is added methyl (triphenylphosphoranylidene) acetate (13.3 g, 40 mmol). The solution is stirred for 72 hours. After this time, the solution is concentrated. The residue is slurried in Et2O. The solution is filtered through a bed of Celite. The collected liquid is concentrated. The residue is purified by column chromatography eluting with a gradient of 50% EtOAc/hexanes to 60% EtOAc/hexanes to give the title compound (4.5 g, 25 mmol) as an oil.

후처리

  1. concentrationAfter this time, the solution is concentrated
  2. filtrationThe solution is filtered through a bed of Celite
  3. concentrationThe collected liquid is concentrated
  4. customThe residue is purified by column chromatography
  5. washeluting with a gradient of 50% EtOAc/hexanes to 60% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-997cf3b78b544914ba3c89f3e3fa0ad6
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06281227B1

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