Methyl Ethyl Ketone → HCID 13290006, compound

HRID 370949Notes

Reaction equation

HRID 370949 reaction equation
[Cl:1][C:2]1[C:3]([OH:13])=[CH:4][C:5]2[C:9]([CH3:10])=[CH:8][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>CN(C)C=O>[Cl:1][C:2]1[C:3]([O:13][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:4][C:5]2[C:9]([CH3:10])=[CH:8][S:7][C:6]=2[C:11]=1[Cl:12]

Participants

5

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 7748Ethyl bromoacetateHCID 13290005HCID 13290005, compound

Product 1

HCID 13290006HCID 13290006, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.7 g of 6,7-dichloro-5-hydroxy-3-methylbenzo[b]thiophene, 4.3 g of ethyl bromoacetate and 20 ml of 2-butanone containing 5 ml of dimethylformamide is stirred at 60°-70° for 2 hours. The cooled mixture is diluted with ice-water and extracted 3 times with ether. The combined ether extract is dried over anhydrous magnesium sulfate and concentrated under vacuum to a brownish oil. Purification of the crude product is effected by column chromatography (alumina/ether). The purified ester is recrystallized from ether-pentane to give 4.3 g of ethyl [(6,7-dichloro-3-methylbenzo[b]thien-5-yl)oxy]acetate as fluffy needles, mp 115°-117°.

Workup

  1. extractionextracted 3 times with ether
  2. extractionThe combined ether extract
  3. dry with materialis dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum to a brownish oil
  5. customPurification of the crude product
  6. customThe purified ester is recrystallized from ether-pentane

Sources & evidence

ORD record
ord-f8ae12620a63491585651e3c81e8fd90
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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