Dimethylformamide → t-Butyl [[6,7-dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl]oxy]acetate

HRID 485899Notes

Reaction equation

HRID 485899 reaction equation
[Cl:1][C:2]1[C:3]([OH:16])=[CH:4][C:5]2[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[OH:11])[S:7][C:6]=2[C:14]=1[Cl:15].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(=O)CC>[Cl:1][C:2]1[C:3]([O:16][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:4][C:5]2[CH:9]=[C:8]([C:10]([OH:11])([CH3:13])[CH3:12])[S:7][C:6]=2[C:14]=1[Cl:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 132900426,7-Dichloro-5-hydroxy-alpha,alpha-dimethylbenzo[b]thiophene-2-methanol

Product 1

HCID 13290043t-Butyl [[6,7-dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl]oxy]acetate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

To a mixture of 6,7-dichloro-5-hydroxy-α,α-dimethylbenzo[b]thiophene-2-methanol in 250 ml of 2-butanone is added a solution of 7.7 g of t-butyl bromoacetate in 50 ml 2-butanone and the resultant mixture is placed in a preheated oil-bath at 95°. To the mixture is added 6.7 g of potassium carbonate and 3 ml of dimethylformamide and the reaction mixture is refluxed at 95° for 21/2 hrs. The cooled mixture is filtered and 100 ml of water is added. The layers are separated and the aqueous phase is extracted two times with ethyl ether. The organic extracts are washed, dried over anhydrous magnesium sulfate, filtered and concentrated to give a solid. Recrystallization from ethyl ether and pentane gives 11.5 g of t-butyl [[6,7-dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl]oxy]acetate, mp 137°-138°.

Workup

  1. temperaturethe reaction mixture is refluxed at 95° for 21/2 hrs
  2. filtrationThe cooled mixture is filtered
  3. addition100 ml of water is added
  4. customThe layers are separated
  5. extractionthe aqueous phase is extracted two times with ethyl ether
  6. washThe organic extracts are washed
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a solid
  11. customRecrystallization from ethyl ether and pentane

Sources & evidence

ORD record
ord-aba10ebf3d28408e8d3fd78e7b375199
Source dataset
uspto-grants-1985_08
Patent number
US04537976

Reaction notes

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