1,2-Dimethoxyethane → 3-Ethyl-5-phenyl-2,3-dihydrobenzothiepine

HRID 1604494노트

반응식

HRID 1604494 반응식
COCCOC.[C:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21][CH2:22][CH:23]([CH2:26][CH3:27])[CH:24]=O)(=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[Zn].O>[CH2:26]([CH:23]1[CH:24]=[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:21][CH2:22]1)[CH3:27]

참가 물질

5

반응물 2

HCID 80711,2-DimethoxyethaneHCID 223252232-((2-Benzoylphenylthio)methyl)butyraldehyde

생성물 1

HCID 223252063-Ethyl-5-phenyl-2,3-dihydrobenzothiepine수율 77.3%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 962Water용매

실험 절차

To a mixture of 2.61 g (0.04 mole) of zinc dust and 60 mL of DME was added 7.5 g (0.048 mole) of TiCl3. The reaction mixture was held at reflux for 2 h. A solution of 2.98 g (0.01 mole) of 11 was added dropwise in 1 h. The reaction mixture was held at reflux for 18 h, cooled and poured into water. The organic was extracted into ether. The ether layer was washed with brine and filtered through Celite. The filtrate was dried over MgSO4 and concentrated. The residual oil (2.5 g) was purified by HPLC to give 2.06 g (77%) of 12 as an oil in the second fraction.

후처리

  1. temperatureat reflux for 2 h
  2. temperatureat reflux for 18 h
  3. temperaturecooled
  4. extractionThe organic was extracted into ether
  5. washThe ether layer was washed with brine
  6. filtrationfiltered through Celite
  7. dry with materialThe filtrate was dried over MgSO4
  8. concentrationconcentrated
  9. customThe residual oil (2.5 g) was purified by HPLC

출처 및 근거

ORD 기록
ord-7feb6c149c4242d8b50b9628e9759fd8
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05994391

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