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

HRID 362179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362179
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1B (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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-ca532c555b4043f0b2c133c4d9e81124
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869426

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