Water → HCID 13340645, compound

HRID 1981309Notes

Reaction equation

HRID 1981309 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.C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28]([O:30][CH3:31])=[O:29].O>CN(C)C=O.CCCCCC>[CH3:31][O:30][C:28](=[O:29])[CH2:27][O:15][C:14](=[O:16])[CH2:13][C:10]1[CH:11]=[CH:12][C:7]2[O:6][CH2:5][C:4]3[CH:17]=[CH:18][S:19][C:3]=3[C:2](=[O:1])[C:8]=2[CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 123447152-(10-oxo-4H-thieno[3,2-c][1]benzoxepin-8-yl)acetic acid

Product 1

HCID 13340645HCID 13340645, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 12.54 g (0.046 m) of 4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-acetic acid in 100 ml of dimethylformamide (DMF) and 3.18 g (0.033 m) of K2CO3 was warmed to 60° C. for 1 hour in an atmosphere of nitrogen. To this mixture 7.7 g (0.05 m) of methyl bromoacetate was added dropwise and the mixture was held at 60° C. overnight (about 16 hours). The reaction mixture was poured into water and extracted with ether. The ether extract was washed with 5% NaHCO3 and water, dried over Na2SO4, filtered and evaporated to give an oil which solidified. Trituration with hexane gave 12.5 g (78%) of methyl(4,10-dihydro-10-oxothieno[3,2-c][1]benzoxepin-8-yl)acetoxyacetate, m.p. 78°-80° C.

Workup

  1. custom(about 16 hours)
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washwas washed with 5% NaHCO3 and water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give an oil which

Sources & evidence

ORD record
ord-1d0f777570a04486b22f3d8cf9c84db3
Source dataset
uspto-grants-1985_04
Patent number
US04514411

Reaction notes

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