Potassium Carbonate → HCID 67017790, compound

HRID 2243182Notes

Reaction equation

HRID 2243182 reaction equation
Cl[C:2]1[CH2:7][CH:6]([CH3:8])[CH2:5][CH2:4][C:3]=1[CH:9]=O.C(=O)([O-])[O-].[K+].[K+].[C:17]([O:21][CH3:22])(=[O:20])[CH2:18][SH:19]>CN(C=O)C>[CH3:22][O:21][C:17]([C:18]1[S:19][C:2]2[CH2:7][CH:6]([CH3:8])[CH2:5][CH2:4][C:3]=2[CH:9]=1)=[O:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 13096046HCID 13096046, compound

Product 1

HCID 67017790HCID 67017790, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

769 mg of the crude 2-chloro-4-methyl-cyclohex-1-enecarbaldehyde obtained in step a) were dissolved in DMF (10 ml). Then 837 mg (6.06 mmol) of potassium carbonate and 440 μl (4.85 mmol) of methyl thioglycolate were added and the mixture was heated to 100° C. for 16 h. After cooling to RT, the solvent was removed in vacuo. Water was added to the remaining residue and the mixture was extracted with ethyl acetate. The organic extracts were then washed with 50% sodium chloride solution, dried (MgSO4) and concentrated to give 704 mg of 6-methyl-4,5,6,7-tetrahydro-benzo[b]thiophene-2-carboxylic acid methyl ester (containing 10% of 4-methyl-4,5,6,7-tetrahydro-benzo[b]thiophene-2-carboxylic acid methyl ester) as dark brown oil. MS (ISP) 211.1 (M+H)+.

Workup

  1. temperatureAfter cooling to RT
  2. customthe solvent was removed in vacuo
  3. additionWater was added to the remaining residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic extracts were then washed with 50% sodium chloride solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c3a9df1c8f124acaa4da92f46cb174c6
Source dataset
uspto-grants-2010_03
Patent number
US07674815B2

Reaction notes

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