Methanol → HCID 13746692, compound

HRID 1731628Notes

Reaction equation

HRID 1731628 reaction equation
[CH2:1]1[C:21]2[C:4](=[CH:5][C:6]3[S:12][C:11]4[CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=[CH:16][C:10]=4[CH2:9][CH2:8][C:7]=3[CH:20]=2)[CH2:3][CH2:2]1.S(=O)(=O)(O)O.[CH3:27]O>>[CH2:1]1[C:21]2[C:4](=[CH:5][C:6]3[S:12][C:11]4[CH:13]=[C:14]([C:17]([O:19][CH3:27])=[O:18])[CH:15]=[CH:16][C:10]=4[CH2:9][CH2:8][C:7]=3[CH:20]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 13746691HCID 13746691, compound

Product 1

HCID 13746692HCID 13746692, compound

Procedure

A suspension of crude 2,3,10,11-tetrahydro-1H-benzo[b]indeno[5,6-f]thiepin-7-carboxylic acid (8.276 g, 28 mmole) in methanol (200 ml) containing concentrated sulfuric acid was stirred under reflux for 20 hours. The suspension was evaporated, water was added and the product was extracted with chloroform. The crude ester was purified by chromatography (250 g Merck silica gel eluted with 1:1 hexane/methylene chloride) The title compound had m.p. 110°-111° C. (from acetonitrile).

Workup

  1. temperatureunder reflux for 20 hours
  2. customThe suspension was evaporated
  3. additionwater was added
  4. extractionthe product was extracted with chloroform
  5. customThe crude ester was purified by chromatography (250 g Merck silica gel eluted with 1:1 hexane/methylene chloride) The title compound

Sources & evidence

ORD record
ord-c15fdf54efad4a0d96e6071d064c69a4
Source dataset
uspto-grants-1986_11
Patent number
US04622403

Reaction notes

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