Dimethylformamide → Methyl (3-benzyloxy-5-trifluoromethylthien-2-yl)-carboxylate

HRID 2229115Notes

Reaction equation

HRID 2229115 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([F:10])([F:9])[F:8])[S:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].CN(C)C=O.[H-].[Na+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[CH2:22]([O:1][C:2]1[CH:6]=[C:5]([C:7]([F:10])([F:8])[F:9])[S:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 2759855Methyl 3-hydroxy-5-(trifluoromethyl)thiophene-2-carboxylate

Product 1

HCID 11278508Methyl (3-benzyloxy-5-trifluoromethylthien-2-yl)-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5B (5.0 g) and dimethylformamide (50 ml) is treated with sodium hydride (1.06 g). Benzylbromide (3.15 ml) was slowly added to the resulting reaction mixture and stirred at room temperature for 20 hours. The reaction mixture was poured into water. The mixture was extracted with diethyl ether twice. The combined organic phases were washed with water, dried and concentrated in vacuo. The crude product was chromatographed (hexane/dichloromethane, 1/1) to give the product as a white solid (4.5 g, 64%) with a melting point of 52-53.5° C.

Workup

  1. extractionThe mixture was extracted with diethyl ether twice
  2. washThe combined organic phases were washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe crude product was chromatographed (hexane/dichloromethane, 1/1)

Sources & evidence

ORD record
ord-b5cb9e4df63d4ecfaed0a57dcba8d298
Source dataset
uspto-grants-2002_07
Patent number
US06420315B1

Reaction notes

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