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

HRID 2199833노트

반응식

HRID 2199833 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d8754f6256774591989d11c928876ce9
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359315B2

반응 노트

불러오는 중…