Potassium Phosphate, Dibasic → ethyl 4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate

HRID 623777노트

반응식

HRID 623777 반응식
[F:1][C:2]([F:8])([F:7])S(Cl)(=O)=O.[CH2:9]([O:11][C:12]([C:14]1[NH:15][CH:16]=[C:17]([CH3:19])[CH:18]=1)=[O:13])[CH3:10].OP([O-])([O-])=O.[K+].[K+]>C(#N)C.CCOC(C)=O.O>[CH3:19][C:17]1[CH:18]=[C:14]([C:12]([O:11][CH2:9][CH3:10])=[O:13])[NH:15][C:16]=1[C:2]([F:8])([F:7])[F:1]

참가 물질

7

반응물 3

HCID 24450Potassium Phosphate, DibasicHCID 79000Trifluoromethanesulfonyl chlorideHCID 643361Ethyl 4-methyl-1H-pyrrole-2-carboxylate

생성물 1

HCID 71502098ethyl 4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate수율 71.13%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

Trifluoromethanesulfonyl chloride (40.7 mL, 381.67 mmol) was added to the argon degassed solution of ethyl-4-methyl-1H-pyrrole-2-carboxylate (40 g, 254.45 mmol), K2HPO4 (132.9 g, 763.35 mmol), dichlorotris(1,10-phenanthroline) ruthenium (II) hydrate (3.6 g, 5.08 mmol) in acetonitrile. The reaction mixture was stirred for 6 d at room temperature adjacent to a fluorescent light bulb (23 W). The reaction mixture was diluted with EtOAc and H2O. The aqueous layer was extracted with EtOAc (2×700 mL). Combined organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure to yield crude mass which was then purified by column chromatography (100-200 mesh Silica gel; 20% ethyl acetate/hexane; Rff-value 0.7) to afford title compound (25 g, 71.13% yield, white color solid).

후처리

  1. extractionThe aqueous layer was extracted with EtOAc (2×700 mL)
  2. dry with materialCombined organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto yield crude mass which
  5. customwas then purified by column chromatography (100-200 mesh Silica gel; 20% ethyl acetate/hexane; Rff-value 0.7)

출처 및 근거

ORD 기록
ord-9dc1cf21e01e44d29b1ec13a8b78558e
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302988B2

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