Methyl 2-chloroacrylate → Methyl 2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carboxylate

HRID 1739537노트

반응식

HRID 1739537 반응식
[F:1][C:2]([F:15])([F:14])[CH2:3][N:4]=[C:5](Cl)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.Cl[C:17](=[CH2:22])[C:18]([O:20][CH3:21])=[O:19].N12CCCN=C1CCCCC2>CN(C)C=O>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([C:5]2[NH:4][C:3]([C:2]([F:15])([F:14])[F:1])=[CH:22][C:17]=2[C:18]([O:20][CH3:21])=[O:19])=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 6659Methyl 2-chloroacrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11807271Benzenecarboximidoyl chloride, 4-chloro-N-(2,2,2-trifluoroethyl)-

생성물 1

HCID 11034029Methyl 2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carboxylate수율 34.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of N-(2,2,2-trifluoroethyl)-4-chloro-benzimidoyl chloride (10.2 g, 0.04 mol) and methyl 2-chloroacrylate (5.8 g, 0.048 mol) in N,N-dimethylformamide is treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DEU, 19.5 g, 0.128 mol) over 30 minutes at such a rate that the temperature is kept at 40° C., stirred for two hours, and quenched with water and ethyl acetate. The organic layer is separated, washed sequentially with aqueous HCl and water, and concentrated in vacuo to obtain an oil. Flash column chromatography of the oil using silica gel and a 20% ethyl acetate in heptane solution and crystallization from heptane gives the title product as white crystals (4.2 g, 34.6% yield, mp 120.0-122.5° C.).

후처리

  1. customis kept at 40° C.
  2. customquenched with water and ethyl acetate
  3. customThe organic layer is separated
  4. washwashed sequentially with aqueous HCl and water
  5. concentrationconcentrated in vacuo
  6. customto obtain an oil
  7. customa 20% ethyl acetate in heptane solution and crystallization from heptane

출처 및 근거

ORD 기록
ord-9b6c1ab50bff4f7592129c8f82bc5e4c
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05965773

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