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

HRID 1837647Notes

Reaction equation

HRID 1837647 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 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.

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-075185b33d71450eb58a362c50da4807
Source dataset
uspto-grants-2004_08
Patent number
US06784201B2

Reaction notes

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