p-Toluenesulfonic acid monohydrate → Methyl 4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-acetate

HRID 1085594Notes

Reaction equation

HRID 1085594 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[C:10]([CH2:13][C:14]([OH:16])=[O:15])[CH:11]=[CH:12][C:7]=2[O:6][CH2:5][C:4]2[CH:17]=[CH:18][S:19][C:3]1=2.O.[C:21]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[O:1]=[C:2]1[C:8]2[CH:9]=[C:10]([CH2:13][C:14]([O:16][CH3:21])=[O:15])[CH:11]=[CH:12][C:7]=2[O:6][CH2:5][C:4]2[CH:17]=[CH:18][S:19][C:3]1=2

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 123447152-(10-oxo-4H-thieno[3,2-c][1]benzoxepin-8-yl)acetic acid

Product 1

HCID 13051081Methyl 4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4,10-Dihydro-10-oxothieno[3,2-c] [1] benzoxepin-8-acetic acid, 25.5 g, synthesized according to the method of D. E. Aultz, et al. [J. Med. Chem., 20, 456 (1977)] and 0.9 g of p-toluenesulfonic acid monohydrate were heated under reflux for 3 hours in 600 ml of methanol. The solvent was distilled off under reduced pressure and the resulting residue was extracted with 500 ml of ethyl acetate. After washing in sequence with saturated sodium bicarbonate aqueous solution and then with saturated sodium chloride aqueous solution, the extract was dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure The resulting residue was subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate=3:1) to give 24.9 g of methyl 4,10-dihydro-10-oxothieno[3,2-c] [1] benzoxepin-8-acetate as light yellow solids.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. extractionthe resulting residue was extracted with 500 ml of ethyl acetate
  3. washAfter washing in sequence with saturated sodium bicarbonate aqueous solution
  4. dry with materialwith saturated sodium chloride aqueous solution, the extract was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure The resulting residue
  6. washwas subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-de7d67772169416990eca7ea8f598446
Source dataset
uspto-grants-1991_04
Patent number
US05010104

Reaction notes

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