Tosylmethyl isocyanide → ethyl 4-(trifluoromethyl)-1H-pyrrole-3-carboxylate

HRID 372963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 372963
CC(C)([O-])C.[K+].[F:7][C:8]([F:17])([F:16])/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12].C1(C)C=CC(S([CH2:27][N+:28]#[C-:29])(=O)=O)=CC=1>O1CCCC1>[F:7][C:8]([F:16])([F:17])[C:9]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:27][NH:28][CH:29]=1

Komponenten

5

Edukt 3

HCID 161915Tosylmethyl isocyanideHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 14370786ethyl 4-(trifluoromethyl)-1H-pyrrole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

A solution of potassium t-butoxide (8.11 g, 0.075 mol) in tetrahydrofuran at -60° C. is treated dropwise with a mixture of ethyl 4,4,4-trifluorocrotonate (10.5 g, 0.063 mol) and p-tolylsulfonylmethylisocyanide (12.2 g, 0.063 mol) in tetrahydrofuran over a 1 hour period, stirred at -60° C. for 30 minutes, allowed to warm to room temperature and quenched with water. The reaction mixture is extracted with ether and ethyl acetate. The combined extracts are washed with brine, dried (MgSO4) and concentrated in vacuo to give a solid residue. Recrystallization from 1,2-dichloroethane affords the title compound as a tan solid, 7.3 g (56%), mp 163°-164° C.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. customquenched with water
  3. extractionThe reaction mixture is extracted with ether and ethyl acetate
  4. washThe combined extracts are washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give a solid residue
  8. customRecrystallization from 1,2-dichloroethane

Quellen und Nachweise

ORD-Eintrag
ord-4895532cb52f432eb6f0a99c3b42bf1b
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05162308

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