Ethanol → HCID 13134777, compound

HRID 355105Notes

Reaction equation

HRID 355105 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:16][C:17]([OH:19])=[O:18].[CH2:20](O)[CH3:21]>O>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

4

Reactant 2

HCID 702EthanolHCID 12443712HCID 12443712, compound

Product 1

HCID 13134777HCID 13134777, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 70 mg of (10,11-dihydro dibenzo[b,f]thiepin-2-yl)-acetic acid was added 3 ml of ethanol containing 7% hydrogen chloride, and the mixture was stirred under a dry atmosphere at room temperature for 2 hours. To this was added water, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated sodium hydrogen carbonate solution and then with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain a residue, which was chromatographed over 7 g of silica gel and eluted with n-hexane/acetone (10/1), thereby yielding 70 mg (yield: 91%) of ethyl (10,11-dihydro dibenzo[b,f]thiepin-2-yl)-acetate as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated sodium hydrogen carbonate solution
  3. dry with materialwith a saturated sodium chloride solution and dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customto obtain a residue, which
  6. customwas chromatographed over 7 g of silica gel
  7. washeluted with n-hexane/acetone (10/1)

Sources & evidence

ORD record
ord-6f948d396fca4a4a9874edbbb8af6c94
Source dataset
uspto-grants-1983_03
Patent number
US04377702

Reaction notes

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