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

HRID 1843957ノート

反応式

HRID 1843957 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 22473847Methyl 5-fluoro-1-benzothiophene-2-carboxylate収率 33.89%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 8058Hexane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5e0a56d21a124533abfb1ce61d0ba034
出典データセット
uspto-grants-2015_02
特許番号
US08946260B2

反応ノート

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