1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-(Trifluoromethyl)benzo[b]thiophene

HRID 1908231ノート

反応式

HRID 1908231 の反応式
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:14]=[CH:13][C:6]2[S:7][C:8](C(O)=O)=[CH:9][C:5]=2[CH:4]=1.N12CCCN=C1CCCCC2>CC(N(C)C)=O.Cl>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:14]=[CH:13][C:6]2[S:7][CH:8]=[CH:9][C:5]=2[CH:4]=1

参加物

5

反応物 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27830435-(Trifluoromethyl)-1-benzothiophene-2-carboxylic acid

生成物 1

HCID 117456995-(Trifluoromethyl)benzo[b]thiophene収率 74.3%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
200 °C

実験手順

A mixture of 5-trifluoromethyl-benzo[b]thiophene-2-carboxylic acid (2.00 g, 8.12 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (5.0 mL, 34 mmol) in DMA (13 mL) was heated via microwave irradiation at 200° C. for 1 h. The reaction was cooled to rt, diluted with HCl (1 N aq., 20 mL) and extracted with EtOAc (20 mL). The organic layer was washed with water (10 mL), dried (Na2SO4) and concentrated. The residue was taken up in Et2O (25 mL) and washed with water (25 mL). The aqueous layer was extracted with Et2O (10 mL×2). The combined Et2O layers were dried (Na2SO4) and concentrated. The crude material was purified (FCC) to yield the title compound (1.22 g, 74%).

後処理

  1. temperatureThe reaction was cooled to rt
  2. extractionextracted with EtOAc (20 mL)
  3. washThe organic layer was washed with water (10 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. washwashed with water (25 mL)
  7. extractionThe aqueous layer was extracted with Et2O (10 mL×2)
  8. dry with materialThe combined Et2O layers were dried (Na2SO4)
  9. concentrationconcentrated
  10. customThe crude material was purified (FCC)

出典と根拠

ORDレコード
ord-0c323f83306e40089a78efb900a26d77
出典データセット
uspto-grants-2013_12
特許番号
US08598202B2

反応ノート

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