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

HRID 591394Notes

Reaction equation

HRID 591394 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[C:10]([CH3:15])=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[S:7][CH:6]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+].[Cl:28][C:29]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:30]=1[CH2:31]Cl>O>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[C:10]([CH3:15])=[CH:11][C:12]([O:14][CH2:31][C:30]3[CH:33]=[CH:34][C:35]([Cl:37])=[CH:36][C:29]=3[Cl:28])=[CH:13][C:8]=2[S:7][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72122,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 121001301Methyl(6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate

Product 1

HCID 118667001Methyl(6-((2,4-dichlorobenzyl)oxy)-4-methyl-1-benzothiophen-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl(6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate (174 mg) and DMF (dry) (2 mL) were added K2CO3 (112 mg) and 2,4-dichlorobenzyl chloride (0.113 mL) at room temperature. After stirring at room temperature for 5 h, the mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, 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 (233 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed 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-05791bf18e7047989d2bf7e71c0caf0c
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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