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

HRID 1935568Notes

Reaction equation

HRID 1935568 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. additionwas added 7.5 g (0.048 mole) of Ticl3
  2. temperatureat reflux for 2 h
  3. temperatureat reflux for 18 h
  4. temperaturecooled
  5. extractionThe organic was extracted into ether
  6. washThe ether layer was washed with brine
  7. filtrationfiltered through Celite
  8. dry with materialThe filtrate was dried over MgSO4
  9. concentrationconcentrated
  10. customThe residual oil (2.5 g) was purified by HPLC

Sources & evidence

ORD record
ord-dca7b1fa8c8d4e9d8274f05d24cb3ef6
Source dataset
uspto-grants-2002_05
Patent number
US06387924B2

Reaction notes

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