Ethyl Acetate → Methyl 5-fluoro-1-benzothiophene-2-carboxylate

HRID 1843957노트

반응식

HRID 1843957 반응식
[SH:1][CH2:2][C:3]([O:5][CH3:6])=[O:4].F[C:8]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:9]=1[CH:10]=O.C(OCC)(=O)C>CC#N.CCCCCC>[F:16][C:13]1[CH:14]=[CH:15][C:8]2[S:1][C:2]([C:3]([O:5][CH3:6])=[O:4])=[CH:10][C:9]=2[CH:12]=1

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 16907Methyl ThioglycolateHCID 1376632,5-Difluorobenzaldehyde

생성물 1

HCID 22473847Methyl 5-fluoro-1-benzothiophene-2-carboxylate수율 33.89%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 8058Hexane용매

실험 절차

TEA (3.705 g, 36.619 mmol) was added to a solution of methyl 2-mercaptoacetate (3.293 g, 30.985 mmol) in CH3CN (12.5 mL). This was followed by the addition of 2,5-difluorobenzaldehyde (4 g, 28.169 mmol) in CH3CN (12.5 mL) and the resulting reaction mass was refluxed overnight under nitrogen atmosphere. The reaction was monitored by TLC (5% ethyl acetate in hexane). The reaction mass was concentrated under reduced pressure to obtain the crude product. Purification by column chromatography on silica gel (15% ethyl acetate in hexane) afforded 2 g of the product (33.89% yield).

후처리

  1. customthe resulting reaction mass
  2. temperaturewas refluxed overnight under nitrogen atmosphere
  3. concentrationThe reaction mass was concentrated under reduced pressure
  4. customto obtain the crude product
  5. customPurification by column chromatography on silica gel (15% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-5e0a56d21a124533abfb1ce61d0ba034
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946260B2

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