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

HRID 23325Notes

Reaction equation

HRID 23325 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-287dfd2038e041b492ddf49b33dafd99
Source dataset
uspto-grants-2005_02
Patent number
US06852673B2

Reaction notes

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