Dimethylformamide → Ethyl(6-((2,4-dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetate

HRID 591390Notes

Reaction equation

HRID 591390 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[S:8][CH:7]=1)[CH3:2].CN(C=O)C.[Cl:22][C:23]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:24]=1[CH2:25]Cl.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:25][C:24]3[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:23]=3[Cl:22])=[CH:14][C:9]=2[S:8][CH:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72122,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 57431998(6-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester

Product 1

HCID 118666999Ethyl(6-((2,4-dichlorobenzyl)oxy)-1-benzothiophen-3-yl)acetateYield 84.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of ethyl(6-hydroxy-1-benzothiophen-3-yl)acetate (11.0 g) and DMF (200 mL) were added 2,4-dichlorobenzyl chloride (10.9 g) and K2CO3 (9.60 g). The mixture was stirred at 20° for 16 h. The mixture was diluted with EtOAc, and washed successively with water and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE) to give the title compound (15.5 g).

Workup

  1. washwashed successively with water and brine
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (EtOAc/PE)

Sources & evidence

ORD record
ord-6380ce19cf6d4cae922849ae5cda88b2
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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