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

HRID 1085594노트

반응식

HRID 1085594 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-de7d67772169416990eca7ea8f598446
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05010104

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