2-(6,6a,7,8,9,10,10a,11-Octahydro-11-oxodibenz[b,e]oxepin-3-yl)propionic acid → Phenethyl 2-(6,6a,7,8,9,10,10a,11-octahydro-11-oxodibenz[b,e]oxepin-3-yl)propionate

HRID 223717Notes

Reaction equation

HRID 223717 reaction equation
[O:1]=[C:2]1[CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]2[CH2:6][O:5][C:4]2[CH:13]=[C:14]([CH:17]([CH3:21])[C:18]([OH:20])=[O:19])[CH:15]=[CH:16][C:3]1=2>S(Cl)(Cl)=O>[O:1]=[C:2]1[CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]2[CH2:6][O:5][C:4]2[CH:13]=[C:14]([CH:17]([CH3:21])[C:18]([O:20][CH2:8][CH2:2][C:3]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:4]=3)=[O:19])[CH:15]=[CH:16][C:3]1=2

Participants

3

Reactant 1

HCID 128325042-(6,6a,7,8,9,10,10a,11-Octahydro-11-oxodibenz[b,e]oxepin-3-yl)propionic acid

Product 1

HCID 12836635Phenethyl 2-(6,6a,7,8,9,10,10a,11-octahydro-11-oxodibenz[b,e]oxepin-3-yl)propionateYield 58.8%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

2-(6,6a,7,8,9,10,10a,11-Octahydro-11-oxodibenz[b,e]oxepin-3-yl)propionic acid (1.0 g) was added to thionyl chloride (10 ml) and the mixture was refluxed with stirring for 2 hours. The excess of thionyl chloride was distilled off under reduced pressure. To the oily residue was added a solution of phenethyl alcohol (2 ml) in xylene (20 ml) and the mixture was heated under reflux for 18 hours, cooled and poured into water. The xylene layers were separated, washed with water, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residue was chromatographed on silica gel, using toluene as an eluent, to give the title compound (0.4 g) as an oil. IR νmaxfilm cm-1 : 1720, 1670 (C=O). HRMS m/e: 392.2007 (M+) (Molecular weight calculated for C25H28O4 : 392.1987).

Workup

  1. temperaturethe mixture was refluxed
  2. distillationThe excess of thionyl chloride was distilled off under reduced pressure
  3. additionTo the oily residue was added a solution of phenethyl alcohol (2 ml) in xylene (20 ml)
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 18 hours
  6. temperaturecooled
  7. additionpoured into water
  8. customThe xylene layers were separated
  9. washwashed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. customevaporated to dryness under reduced pressure
  12. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-8ef6069b054940c8bfbd37646d182226
Source dataset
uspto-grants-1982_10
Patent number
US04356186

Reaction notes

Loading…