Dimethylformamide → HCID 89767477, compound

HRID 591483Notes

Reaction equation

HRID 591483 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C([O-])([O-])=O.[K+].[K+].[Cl:16][C:17]1[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:18]=1[CH2:19][O:20][C:21]1[CH:35]=[CH:34][C:24]2[C:25]([OH:33])=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[S:27][C:23]=2[CH:22]=1.CN(C=O)C>O>[C:6]([O:5][C:3](=[O:4])[CH2:2][O:33][C:25]1[C:24]2[CH:34]=[CH:35][C:21]([O:20][CH2:19][C:18]3[CH:36]=[CH:37][C:38]([Cl:40])=[CH:39][C:17]=3[Cl:16])=[CH:22][C:23]=2[S:27][C:26]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 89767819HCID 89767819, compound

Product 1

HCID 89767477HCID 89767477, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of t-butyl bromoacetate (0.736 mL), K2CO3 (0.626 g), ethyl 6-((2,4-dichlorobenzyl)oxy)-3-hydroxy-1-benzothiophene-2-carboxylate (1.8 g) and DMF (20 mL) was stirred at room temperature for 20 h. Water was added to the mixture and the mixture was extracted with EtOAc. The EtOAc extract was washed successively with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (1.330 g). The obtained crystals were recrystallized from acetone-hexane.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. extractionThe EtOAc extract
  3. washwas washed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-83e51ea2b5cb42a8a4cbc74f1111583e
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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