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

HRID 2419757Notes

Reaction equation

HRID 2419757 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.S(=O)(=O)(O)O.[CH3:25]O>>[O:1]=[C:2]1[C:8]2[CH:9]=[C:10]([CH2:13][C:14]([O:16][CH3:25])=[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 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 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

Procedure

A mixture of 0.70 g of 4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-acetic acid (Example 1), 8 ml of concentrated sulfuric acid, and 150 ml of methanol is refluxed for 16 hours. The reaction mixture is concentrated in vacuo, diluted with water and extracted with benzene. The combined benzene extracts are washed with 5% sodium hydroxide and water, dried, filtered and concentrated in vacuo to an oil which solidifies upon standing. The solid is recrystallized from methanol to provide light yellow crystals, mp 80°-81° C. of methyl 4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-acetate.

Workup

  1. temperatureis refluxed for 16 hours
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with benzene
  5. washThe combined benzene extracts are washed with 5% sodium hydroxide and water
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to an oil which
  9. customThe solid is recrystallized from methanol

Sources & evidence

ORD record
ord-6253179ff7ea47d2972a8cf025f205d3
Source dataset
uspto-grants-1978_08
Patent number
US04107321

Reaction notes

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