Methyl Ethyl Ketone → HCID 13290023, compound

HRID 1903458Notes

Reaction equation

HRID 1903458 reaction equation
[Cl:1][C:2]1[C:3]([OH:13])=[CH:4][C:5]2[CH:9]=[C:8]([CH3:10])[S:7][C:6]=2[C:11]=1[Cl:12].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].CC(=O)CC.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][O:13][C:3]1[C:2]([Cl:1])=[C:11]([Cl:12])[C:6]2[S:7][C:8]([CH3:10])=[CH:9][C:5]=2[CH:4]=1)[CH3:20]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 7748Ethyl bromoacetateHCID 516892Sodium BicarbonateHCID 13290022HCID 13290022, compound

Product 1

HCID 13290023HCID 13290023, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.1 g of 6,7-dichloro-5-hydroxy 2-methylbenzo[b]thiophene, 1.88 g of ethyl bromoacetate, 20 ml of 2-butanone, 2 ml of dimethylformamide and 4.0 g of sodium bicarbonate is refluxed for 16 hours. The cooled mixture is diluted with ice, extracted 3 times with ether and the ether solution is washed, dried and concentrated. The crude oil after removal of solvent is purified by passing it through an alumina column. Elution with ether gives 2.7 g of ethyl[ (6,7-dichloro-2-methylbenzo[b]thien-5-yl)oxy]acetate as off-white crystals, mp 91°-92°. An analytical sample is recrystallized twice from hexane and dried at 80°.

Workup

  1. temperatureis refluxed for 16 hours
  2. additionThe cooled mixture is diluted with ice
  3. extractionextracted 3 times with ether
  4. washthe ether solution is washed
  5. customdried
  6. concentrationconcentrated
  7. customThe crude oil after removal of solvent
  8. customis purified
  9. washElution with ether

Sources & evidence

ORD record
ord-af868ca874e446c5b4535f5ac64f9d47
Source dataset
uspto-grants-1984_03
Patent number
US04436748

Reaction notes

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