Dimethylformamide → Ethyl [(6,7-dichloro-2-(1-hydroxyethyl)benzo[b]thien-5-yl)oxy]acetate

HRID 652685Notes

Reaction equation

HRID 652685 reaction equation
[Cl:1][C:2]1[C:3]([OH:15])=[CH:4][C:5]2[CH:9]=[C:8]([CH:10]([CH3:12])[OH:11])[S:7][C:6]=2[C:13]=1[Cl:14].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(=O)CC>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][O:15][C:3]1[C:2]([Cl:1])=[C:13]([Cl:14])[C:6]2[S:7][C:8]([CH:10]([OH:11])[CH3:12])=[CH:9][C:5]=2[CH:4]=1)[CH3:22]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 134776546,7-Dichloro-5-hydroxy-alpha-methylbenzo[b]thiophene-2-methanol

Product 1

HCID 13290073Ethyl [(6,7-dichloro-2-(1-hydroxyethyl)benzo[b]thien-5-yl)oxy]acetateYield 86.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

To a solution of 17 g of 6,7-dichloro-5-hydroxy-α-methylbenzo[b]thiophene-2-methanol in 250 ml of 2-butanone is added a solution of 11.8 g of ethyl bromoacetate in 50 ml 2-butanone and the mixture is heated at 95°. To the mixture is added 12 g of potassium carbonate and 5.3 ml of dimethylformamide and the reaction mixture is refluxed at 100° for 21/2 hrs. The cooled mixture is filtered and 100 ml of water is added. The aqueous phase is extracted two times with ethyl ether. The ether extracts are washed, dried over anhydrous magnesium sulfate, filtered and concentrated to give a solid. Recrystallization from acetone and hexane gives 19.5 g of ethyl[(6,7-dichloro-2-(1-hydroxyethyl)benzo[b]thien-5-yl)oxy]acetate, mp 101°-103°.

Workup

  1. temperaturethe mixture is heated at 95°
  2. temperaturethe reaction mixture is refluxed at 100° for 21/2 hrs
  3. filtrationThe cooled mixture is filtered
  4. addition100 ml of water is added
  5. extractionThe aqueous phase is extracted two times with ethyl ether
  6. washThe ether extracts are washed
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a solid
  11. customRecrystallization from acetone and hexane

Sources & evidence

ORD record
ord-8546328d698b460693c1df5086df3736
Source dataset
uspto-grants-1987_06
Patent number
US04672138

Reaction notes

Loading…