Dimethylformamide → HCID 13290052, compound

HRID 652674Notes

Reaction equation

HRID 652674 reaction equation
[Cl:1][C:2]1[C:3]([OH:18])=[CH:4][C:5]2[CH:9]=[C:8]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[S:7][C:6]=2[C:16]=1[Cl:17].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:1][C:2]1[C:3]([O:18][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:4][C:5]2[CH:9]=[C:8]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[S:7][C:6]=2[C:16]=1[Cl:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 13290051HCID 13290051, compound

Product 1

HCID 13290052HCID 13290052, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

To a mixture of 6,7-dichloro-2-cyclohexyl-5-hydroxybenzo[b]thiophene and 110 ml of 2-butanone is added 11.5 g of ethyl bromoacetate in 60 ml of 2-butanone, followed by 10 ml dimethylformamide and 9.5 g of potassium carbonate. The reaction mixture is stirred under nitrogen at 90°-95° for 3 hrs, allowed to cool and filtered. The filtrate is poured into a mixture of 100 ml water and 100 ml ether. The layers are separated and the aqueous layer is extracted with 200 ml of ether. The organic layers are combined dried over anhydrous magnesium sulfate, filtered and the solvent is removed to give a solid which is recrystallized in ether-hexane to give 14.8 g of ethyl [(6,7-dichloro-2-cyclohexylbenzo[b]thien-5-yl)oxy]acetate, mp 73°-75°.

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. additionThe filtrate is poured into a mixture of 100 ml water and 100 ml ether
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with 200 ml of ether
  6. dry with materialThe organic layers are combined dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is removed
  9. customto give a solid which
  10. customis recrystallized in ether-hexane

Sources & evidence

ORD record
ord-1fd477677c6f4f0caa34e9541dfa9a1a
Source dataset
uspto-grants-1987_06
Patent number
US04672138

Reaction notes

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