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

HRID 496162Notes

Reaction equation

HRID 496162 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

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 solutiom 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.

Workup

  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

Sources & evidence

ORD record
ord-03f29a4a957b485f8a33303d2853d1a9
Source dataset
uspto-grants-2005_09
Patent number
US06943189B2

Reaction notes

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