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

HRID 1432871노트

반응식

HRID 1432871 반응식
[Cl:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.C1(P(=[CH:28][C:29]([O:31][CH3:32])=[O:30])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:32][O:31][C:29](=[O:30])/[CH:28]=[CH:7]/[C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1

참가 물질

4

반응물 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 817002-Thiophenecarboxaldehyde, 5-chloro-

생성물 1

HCID 69024911Methyl 3-(5-chlorothiophen-2-yl)prop-2-enoate수율 87.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 5-chloro-2-thiophene-carboxaldehyde (5.10 g, 34.8 mmol) in 100 mL of dry CH2Cl2 is added methyl (triphenylphosphoranylidene)acetate (11.8 g, 35.3 mmol). The resulting brown-green mixture is stirred for 19 h at room temperature. The mixture is filtered through a Celite pad, concentrated in vacuo and triturated with hexane. The white precipitate (triphenylphosphine oxide) is filtered off and the filtrate is concentrated. The crude residue is purified via flash column chromatography eluting with a gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes to provide the title compound (6.20 g, 30.6 mmol) as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ7.65 (d, 1H), 7.05 (d, 1H), 6.89 (d, 1H), 6.10 (d, 1H), 3.80 (s, 3H).

후처리

  1. filtrationThe mixture is filtered through a Celite pad
  2. concentrationconcentrated in vacuo
  3. customtriturated with hexane
  4. filtrationThe white precipitate (triphenylphosphine oxide) is filtered off
  5. concentrationthe filtrate is concentrated
  6. customThe crude residue is purified via flash column chromatography
  7. washeluting with a gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-c9c57ca99b3f45578bf5728c533a3cc4
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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