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Ethyl trifluoroacetate → 2,2,2-Trifluoro-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-one

HRID 1456330
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HRID 1456330 반응식
C([Li])CCC.[CH3:6][C:7]1[N:8]=[CH:9][S:10][CH:11]=1.[F:12][C:13]([F:20])([F:19])[C:14](OCC)=[O:15].[Cl-].[NH4+]>O1CCCC1>[CH3:6][C:7]1[N:8]=[C:9]([C:14](=[O:15])[C:13]([F:20])([F:19])[F:12])[S:10][CH:11]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 9794Ethyl trifluoroacetateHCID 127484-MethylthiazoleHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

생성물 1

HCID 221066902,2,2-Trifluoro-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

n-Butyllithium (2.5M solution in hexanes, 40.4 ml) was added dropwise to a stirred solution of 4-methylthiazole (l10 g) in anhydrous tetrahydrofuran at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, ethyl trifluoroacetate (12 ml) was added dropwise. After a further 2 hours the mixture was allowed to warm to room temperature and was, then left stirring overnight. Saturated aqueous ammonium chloride solution was added and the organic phase was separated, dried and evaporated to dryness. The residue was purified by flash chromatography to give the hydrate corresponding to the title compound as a white solid. M.p. 77°-81° C. 13C Nmr (d6 -DMSO) 16.4, 91.1 (q J 32 Hz), 116.3, 122.2 (q, J 287 Hz), 152.0 and 166.6 ppm.

후처리

  1. waitAfter a further 2 hours the mixture was allowed
  2. waitleft
  3. customthe organic phase was separated
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-15fdd352d5e04da084397ec300310c60
출처 데이터셋
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05843971

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