Methyl 3-oxovalerate → Methyl 1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetate

HRID 2270452Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2270452
[CH3:1][CH2:2][C:3]1[C:8]2[NH:9][CH:10]=[C:11]([CH2:12][CH2:13][OH:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1.O=[C:16]([CH2:22][CH3:23])[CH2:17][C:18]([O:20][CH3:21])=[O:19]>Cl>[CH2:22]([C:16]1([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:10]2[NH:9][C:8]3[C:7]([C:11]=2[CH2:12][CH2:13][O:14]1)=[CH:6][CH:5]=[CH:4][C:3]=3[CH2:2][CH3:1])[CH3:23]

Komponenten

4

Edukt 2

HCID 121699Methyl 3-oxovalerateHCID 1982317-Ethyltryptophol

Produkt 1

HCID 527310Methyl 1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetateAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
27.5 °C

Versuchsvorschrift

To a solution of 7-ethyltryptophol (12.0 g) in 1-butanolic hydrogen chloride (5% w/v, 100.0 ml), methyl 3-oxopentanoate (9.1 g) was added in one lot, at 25° C. The reaction mixture was stirred at 25-30° C. for 7 hours. The reaction mixture was extracted with hexane (100.0 ml). Hexane was concentrated to about 20 ml and methanol (10 ml) was added. The product was filtered, washed with methanol and dried to afford the titled compound (14.7 g, 79%), m.p. 128-130° C.; purity: 96.2%.

Aufarbeitung

  1. extractionThe reaction mixture was extracted with hexane (100.0 ml)
  2. concentrationHexane was concentrated to about 20 ml and methanol (10 ml)
  3. additionwas added
  4. filtrationThe product was filtered
  5. washwashed with methanol
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a2dc2fd1d57d472e8baa07739226bfe8
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06331638B1

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