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

HRID 478885Notes

Reaction equation

HRID 478885 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-d1a50c0690c34b7c8ccd0a8c39d8f1b4
Source dataset
uspto-grants-2003_11
Patent number
US06642268B2

Reaction notes

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