Benzene, (diazomethyl)- → HCID 18358879, Verbindung

HRID 428441

Reaktionsgleichung

Reaktionsgleichung von HRID 428441
[C:1]1([CH:7]=[N+:8]=[N-:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([OH:25])[C:18]#[C:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:13]([N+:26]([O-:28])=[O:27])[CH:12]=1>C1COCC1>[C:1]1([C:7]2[C:18]([CH:17]([C:14]3[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][C:13]=3[N+:26]([O-:28])=[O:27])[OH:25])=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 136601Benzene, (diazomethyl)-HCID 18358875Ethyl 4-(4-chloro-2-nitrophenyl)-4-hydroxy-2-butynoate

Produkt 1

HCID 18358879HCID 18358879, VerbindungAusbeute 29,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of freshly generated phenyldiazomethane (2.44 g, 20.7 mmol) in 10 mL of anhydrous THF was added to ethyl 4-(4-chloro-2-nitrophenyl)-4-hydroxy-2-butynoate (5.86 g, 20.7 mmol) in 10 mL THF and the mixture was stirred at room temperature for 18 hours. The reaction mixture was quenched with excess ethereal acetic acid and concentrated via rotary evaporation to an oil (12.24 g) which solidified on cooling. This was filtered to yield the title compound as a pale yellow solid (2.42 g). The filtrate was concentrated via rotary evaporation to an oil which was triturated with hexane:ethyl acetate (4:1) to yield an additional 1.52 g of the title compound (48% combined yield).

Aufarbeitung

  1. customThe reaction mixture was quenched with excess ethereal acetic acid
  2. concentrationconcentrated via rotary evaporation to an oil (12.24 g) which
  3. temperatureon cooling
  4. filtrationThis was filtered

Quellen und Nachweise

ORD-Eintrag
ord-ebd4aa3b0e114d51a7dcbb6e422f01b2
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313290B1

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