p-Toluenesulfonic acid → (E)-4,5-dimethoxy-2-(4-((trifluoromethyl)thio)benzylidene)-2,3-dihydro-1H-inden-1-one

HRID 2199833ノート

反応式

HRID 2199833 の反応式
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:14].[F:15][C:16]([F:27])([F:26])[S:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5]/[C:6](=[CH:22]\[C:21]1[CH:24]=[CH:25][C:18]([S:17][C:16]([F:27])([F:15])[F:26])=[CH:19][CH:20]=1)/[C:7]2=[O:14]

参加物

6

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 2404464,5-Dimethoxy-1-indanoneHCID 27778464-[(Trifluoromethyl)sulfanyl]benzaldehyde

生成物 1

HCID 117940284(E)-4,5-dimethoxy-2-(4-((trifluoromethyl)thio)benzylidene)-2,3-dihydro-1H-inden-1-one

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

To a solution of 4,5-dimethoxy-2,3-dihydro-1H-inden-1-one (165) (100 mg, 0.520 mmol) in toluene 15 mL was added 4-((trifluoromethyl)thio)benzaldehyde (72) (118.4 mg, 0.572 mmol) and PTSA (178.9 mg, 1.414 mmol). The reaction was stirred at 120° C. for 6 h. The resulting reaction mixture was diluted with ethyl acetate and washed with water (3×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted at 25% ethyl acetate in hexane to afford yellow coloured solid of (E)-4,5-dimethoxy-2-(4-((trifluoromethyl)thio)benzylidene)-2,3-dihydro-1H-inden-1-one intermediate 166.

後処理

  1. customThe resulting reaction mixture
  2. washwashed with water (3×25 mL)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated
  5. customto get the crude, which
  6. customwas purified through flash chromatography
  7. washThe compound was eluted at 25% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-d8754f6256774591989d11c928876ce9
出典データセット
uspto-grants-2016_06
特許番号
US09359315B2

反応ノート

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