Dimethylformamide → HCID 13290046, compound

HRID 652669Notes

Reaction equation

HRID 652669 reaction equation
[Cl:1][C:2]1[C:3]([OH:16])=[CH:4][C:5]2[CH:9]=[C:8]([CH:10]([CH2:12][CH3:13])[OH:11])[S:7][C:6]=2[C:14]=1[Cl:15].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(=O)CC>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][O:16][C:3]1[C:2]([Cl:1])=[C:14]([Cl:15])[C:6]2[S:7][C:8]([CH:10]([OH:11])[CH2:12][CH3:13])=[CH:9][C:5]=2[CH:4]=1)[CH3:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 132900456,7-Dichloro-5-hydroxy-alpha-ethylbenzo[b]thiophene-2-methanol

Product 1

HCID 13290046HCID 13290046, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

To a mixture of 6,7-dichloro-5-hydroxy-α-ethylbenzo[b]thiophene-2-methanol and 200 ml of 2-butanone is added a mixture of 7.35 g of ethyl bromoacetate in 100 ml of 2-butanone, followed by 7.4 g of potassium carbonate and 3.3 ml of sieve-dried dimethylformamide. The reaction mixture is stirred at 95°-100° for 3 hrs, allowed to cool and filtered. To the filtrate is added 100 ml of water and the mixture is extracted with ethyl ether. The organic layers are washed, dried over anhydrous magnesium sulfate, filtered and the solvent removed to give an oil which solidifies on cooling. Recrystallization from ethyl ether and hexane gives 10 g of ethyl[(6,7-dichloro-2-(1-hydroxypropyl]benzo[b]thien-5-yl]oxy]acetate, mp 69°-70°.

Workup

  1. additionis added
  2. temperatureto cool
  3. filtrationfiltered
  4. additionTo the filtrate is added 100 ml of water
  5. extractionthe mixture is extracted with ethyl ether
  6. washThe organic layers are washed
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed
  10. customto give an oil which
  11. temperatureon cooling
  12. customRecrystallization from ethyl ether and hexane

Sources & evidence

ORD record
ord-ebe3346a0c174369aa0a0cb042df24af
Source dataset
uspto-grants-1987_06
Patent number
US04672138

Reaction notes

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