Water → 3-Benzylpyrrolylmethyl 2-(5-trifluoromethyl-2-benzothienyl)-3-methylbutanoate

HRID 27946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 27946
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([CH:11]([CH:15]([CH3:17])[CH3:16])[C:12]([OH:14])=[O:13])=[CH:8][C:7]=2[CH:18]=1.S(Cl)(Cl)=O.[CH2:25]([C:32]1[CH:36]=[CH:35][NH:34][C:33]=1[CH2:37]O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>CN(C=O)C.C1C=CC=CC=1.CN(C)C1C=CN=CC=1>[F:20][C:2]([F:19])([F:1])[C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([CH:11]([CH:15]([CH3:17])[CH3:16])[C:12]([O:14][CH2:37][C:33]3[NH:34][CH:35]=[CH:36][C:32]=3[CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:13])=[CH:8][C:7]=2[CH:18]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 539457852-(5-Trifluoromethyl-2-benzothienyl)-3-methylbutanoic acidHCID 543430813-Benzyl-1-pyrrolylmethanol

Produkt 1

HCID 542765353-Benzylpyrrolylmethyl 2-(5-trifluoromethyl-2-benzothienyl)-3-methylbutanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 142844-(Dimethylamino)pyridineKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of 2-(5-trifluoromethyl-2-benzothienyl)-3-methylbutanoic acid (3.95 mmol), thionyl chloride (0.342 ml, 4.74 mmol) and DMF (several drops) in 50 ml benzene is stirred at RT for 2 days. The solvent and excess thionyl chloride are evaporated under reduced pressure. The resulting acid chloride is dissolved in 50 ml benzene, and 3-benzylpyrrolylmethyl alcohol (3.95 mmol) and 0.482 g 4-dimethylaminopyridine (3.95 mmol) are added. The mixture is left at 25° for 18 hours and then heated under reflux for 2 hours. The mixture is then poured into water and extracted with ether. The organic phase is washed with dilute HCL, sat. NaHCO3, water and brine, dried and solvent removed under vacuum to yield 3-benzylpyrrolylmethyl 2-(5-trifluoromethyl-2-benzothienyl)-3-methylbutanoate.

Aufarbeitung

  1. customThe solvent and excess thionyl chloride are evaporated under reduced pressure
  2. dissolutionThe resulting acid chloride is dissolved in 50 ml benzene
  3. waitThe mixture is left at 25° for 18 hours
  4. temperatureheated
  5. temperatureunder reflux for 2 hours
  6. extractionextracted with ether
  7. washThe organic phase is washed with dilute HCL, sat. NaHCO3, water and brine
  8. customdried
  9. customsolvent removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c40e7b1588574efd95d601e70ef488b0
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04224330

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