Methyl Ethyl Ketone → HCID 13290071, compound

HRID 1903509Notes

Reaction equation

HRID 1903509 reaction equation
[Cl:1][C:2]1[C:3]([OH:15])=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][CH2:11][CH3:12])[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+].CC(=O)CC>CN(C)C=O>[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]([CH2:10][CH2:11][CH3:12])=[CH:9][C:5]=2[CH:4]=1)[CH3:22]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 13290070HCID 13290070, compound

Product 1

HCID 13290071HCID 13290071, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 11.5 g of 6,7-dichloro-5-hydroxy-2-n-propylbenzo[b]thiophene, 8.82 g of ethyl bromoacetate, 7.52 g of potassium carbonate, 135 ml of 2-butanone and 9 ml of dimethylformamide is stirred for 3 days. The reaction mixture is filtered and 100 ml of water and 100 ml of ether are added. The layers are separated and the aqueous layer is extracted 2 times with 100-ml portions of ether. The combined organic layers are dried, filtered and the filtrate is evaporated to give an oil which crystallizes from hexane. Recrystallization from ether-hexane gives 9 g of ethyl[ (6,7-dichloro-2-n-propylbenzo[b]thien-5-yl)oxy]acetate, mp 62°-63°.

Workup

  1. filtrationThe reaction mixture is filtered
  2. addition100 ml of water and 100 ml of ether are added
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted 2 times with 100-ml portions of ether
  5. customThe combined organic layers are dried
  6. filtrationfiltered
  7. customthe filtrate is evaporated
  8. customto give an oil which
  9. customcrystallizes from hexane
  10. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-399ae6d2a6ff4148870f36f4baa54c2b
Source dataset
uspto-grants-1984_03
Patent number
US04436748

Reaction notes

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