Methyl Ethyl Ketone → HCID 13290023, compound

HRID 370958Notes

Reaction equation

HRID 370958 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-f0234be965554689a1ca30500540ee5c
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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