Tetrahydrofuran → 6-Benzyloxy-3-(3-(methoxycarbonyl)benzylidene)-4-chromanone

HRID 487902Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 487902
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][CH2:14][CH2:13][C:12]2=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O)([O:22][CH3:23])=[O:21].N1CCCC1.O1CCCC1>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][CH2:14][C:13](=[CH:27][C:26]1[CH:29]=[CH:30][CH:31]=[C:24]([C:20]([O:22][CH3:23])=[O:21])[CH:25]=1)[C:12]2=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 31268PyrrolidineHCID 639145Methyl 3-formylbenzoateHCID 144227766-(Benzyloxy)chroman-4-one

Produkt 1

HCID 545635856-Benzyloxy-3-(3-(methoxycarbonyl)benzylidene)-4-chromanoneAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 17 g of 6-benzyloxy-4-chromanone, 11.3 g of 3-carbomethoxybenzaldehyde, 14.4 g of pyrrolidine, 100 ml of tetrahydrofuran and 300 ml of methanol was stirred at room temperature overnight. The volatiles were evaporated in vacuo to afford the crude product, which was purified by column chromatography on silica gel eluting with dichloromethane. The product fractions were combined and concentrated to an oil which crystallized upon trituration with methanol to give 17.2 g of title product, mp 109°-112° C.

Aufarbeitung

  1. customThe volatiles were evaporated in vacuo
  2. customto afford the crude product, which
  3. customwas purified by column chromatography on silica gel eluting with dichloromethane
  4. concentrationconcentrated to an oil which
  5. customcrystallized upon trituration with methanol

Quellen und Nachweise

ORD-Eintrag
ord-e3f428a8e61049e9aa2a24bff57e741b
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05298512

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