Potassium Carbonate → 4,5-Dihydro-6-oxa-3-thia-benzo[e]azulene-2-carboxylic acid ethyl ester

HRID 84619Notes

Reaction equation

HRID 84619 reaction equation
Cl[C:2]1[CH2:8][CH2:7][O:6][C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[C:3]=1[CH:13]=O.[SH:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.C(OCC)(=O)C>[CH2:20]([O:19][C:17]([C:16]1[S:15][C:2]2[CH2:8][CH2:7][O:6][C:5]3[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=3[C:3]=2[CH:13]=1)=[O:18])[CH3:21]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 579003964-Chloro-2,3-dihydro-benzo[b]oxepine-5-carbaldehyde

Product 1

HCID 579001364,5-Dihydro-6-oxa-3-thia-benzo[e]azulene-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-2,3-dihydro-benzo[b]oxepine-5-carbaldehyde (605 mg, 5.8 mmol) in dimethyl formamide (8 ml) at 0° C., was added ethyl 2-mercaptoacetate (640 μl, 5.8 mmol) and potassium carbonate (800 mg, 5.8 mmol). The reaction mixture was stirred at room temperature for 30 minutes and then at 70° C. for 2 hours. The reaction mixture was cooled and diluted with water and ethyl acetate, and the organic phase was washed with brine, dried (MgSO4), and concentrated in-vacuo. Purification on silica gave 4,5-dihydro-6-oxa-3-thia-benzo[e]azulene-2-carboxylic acid ethyl ester.

Workup

  1. waitat 70° C. for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. washthe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in-vacuo
  6. customPurification on silica

Sources & evidence

ORD record
ord-15fb5c121be043e0aa9f19ab475c9549
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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