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

HRID 1639128ノート

反応式

HRID 1639128 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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
  6. washThe resulting residue was subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-8891b6b336d64a13b4e951fc5451f750
出典データセット
uspto-grants-1989_11
特許番号
US04882351

反応ノート

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