1,8-Diazabicyclo(5.4.0)undec-7-ene → Ethyl 3-methyl-1H-pyrrole-2-carboxylate

HRID 1724790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1724790
[CH2:1]([O:3][C:4]([CH:6]1[C:10]([CH3:11])=[CH:9][CH2:8][N:7]1S(C1C=CC(C)=CC=1)(=O)=O)=[O:5])[CH3:2].C1CCN2C(=NCCC2)CC1>C1COCC1.CCOCC>[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[CH:9][C:10]=1[CH3:11])=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15747141Ethyl 3-methyl-1-(4-methylphenyl)sulfonyl-2,5-dihydropyrrole-2-carboxylate

Produkt 1

HCID 5324582Ethyl 3-methyl-1H-pyrrole-2-carboxylateAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Pyrroline 83 (8.80 g, 28.48 mmol) was dissolved in THF (70 mL). DBU (9.78 mL, 65.50 mmol) was added dropwise and the resulting solution stirred under reflux overnight. The mixture was cooled to room temperature, diluted with ether and washed with 5% aq. HCl, 5% sodium bicarbonate solution and water. The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure to give the crude solid 84 (4.30 g, 98%). 1H-NMR (400 MHz, CDCl3): δ 1.37 (t, 3H), 2.35 (s, 3H), 4.31 (q, 2H), 6.08 (d, 1H), 6.81 (d, 1H), 8.90 (s broad, 1H) ppm. 13C-NMR (100 MHz, CDCl3): δ 12.76, 14.53, 59.96, 112.58, 119.35, 121.53, 127.96, 162.01 ppm. DEPT (100 MHz, CDCl3): CH3 carbons: 12.76, 14.53; CH2 carbons: 59.96; CH carbons: 112.58, 121.53 ppm. LC/MS: 90.74%, m/z=153.

Aufarbeitung

  1. temperatureunder reflux overnight
  2. washwashed with 5% aq. HCl, 5% sodium bicarbonate solution and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ac9dddab0ceb438a97dadb96fd12f59f
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07488747B2

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