Sulfuric Acid → HCID 12832515, compound

HRID 223716Notes

Reaction equation

HRID 223716 reaction equation
[O:1]=[C:2]1[CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]2[CH2:6][S: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(=O)(=O)(O)O.[CH2:27](O)[CH:28]=[CH2:29]>O>[O:1]=[C:2]1[CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]2[CH2:6][S:5][C:4]2[CH:13]=[C:14]([CH:17]([CH3:21])[C:18]([O:20][CH2:29][CH:28]=[CH2:27])=[O:19])[CH:15]=[CH:16][C:3]1=2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7858Allyl AlcoholHCID 30670672-(11-Oxo-6,6a,7,8,9,10,10a,11-octahydrodibenzo[b,e]thiepin-3-yl)propanoic acid

Product 1

HCID 12832515HCID 12832515, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-(6,6a,7,8,9,10,10a,11-octahydro-11-oxodibenzo[b,e]thiepin-3-yl)propionic acid (2.0 g) in allyl alcohol (20 ml) was added concentrated sulfuric acid (1 ml) and the mixture was heated under reflux for one hour in an oil bath maintained at 110° C. The reaction mixture was diluted with water and extracted with toluene. The toluene layers were 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 (1.2 g) as an oil. IR νmaxfilm cm-1 : 1720, 1670 (C=O). HRMS m/e: 344.1415 (Molecular weight calculated for C20H24O3S: 344.1445).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one hour in an oil bath
  3. extractionextracted with toluene
  4. washThe toluene layers were washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-ccf1e0c8766545e380c81e903ac82180
Source dataset
uspto-grants-1982_10
Patent number
US04356186

Reaction notes

Loading…