Hydrochloric Acid → (1E,6E)-1-(1H-indol-6-yl)-7-[2-methoxy-4-(2-tetrahydrofuranylmethoxy)phenyl]hepta-1,6-diene-3,5-dione

HRID 1056811

Reaktionsgleichung

Reaktionsgleichung von HRID 1056811
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=[CH:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15])[CH:8]=2)[CH:3]=[CH:2]1.[B]=O.[CH3:20][O:21][C:22]1[CH:29]=[C:28]([O:30][CH2:31][CH:32]2[CH2:36][CH2:35][CH2:34][O:33]2)[CH:27]=[CH:26][C:23]=1[CH:24]=O.B(OC(C)C)(OC(C)C)OC(C)C.N1CCCCC1.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.[Cl-].[Na+].O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[CH:11]/[C:12](=[O:17])[CH2:13][C:14](=[O:16])/[CH:15]=[CH:24]/[C:23]3[CH:26]=[CH:27][C:28]([O:30][CH2:31][CH:32]4[CH2:36][CH2:35][CH2:34][O:33]4)=[CH:29][C:22]=3[O:21][CH3:20])[CH:8]=2)[CH:3]=[CH:2]1

Komponenten

10

Edukt 7

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 21531Triisopropyl borateHCID 516892Sodium BicarbonateHCID 6327189Boron monoxideHCID 671071096-(1H-indol-6-yl)hex-5-ene-2,4-dioneHCID 867132112-Methoxy-4-(2-tetrahydrofuranylmethoxy)benzaldehyde

Produkt 1

HCID 86713212(1E,6E)-1-(1H-indol-6-yl)-7-[2-methoxy-4-(2-tetrahydrofuranylmethoxy)phenyl]hepta-1,6-diene-3,5-dioneAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

In a 20 mL reaction vessel were placed 19.3 mg (85.0 μmol) of 6-(1H-indol-6-yl)hex-5-ene-2,4-dione and 22 mg (0.32 mol) of boron oxide and they were dissolved in 0.4 mL of ethyl acetate. To the mixture under stirring at 70° C., 20 mg (85 μmol) of 2-methoxy-4-(2-tetrahydrofuranylmethoxy)benzaldehyde and 32 μL (0.14 mmol) of triisopropyl borate were sequentially added. After the mixture was stirred at the same temperature for 1 hour, 18 μL (0.18 mmol) of piperidine was added and the mixture was further stirred for 1 hour. To the reaction mixture was added a 1:1 solution (2 mL) of 1 N hydrochloric acid and saturated brine at room temperature and the mixture was stirred for 5 minutes to 1 hour (further, the mixture was neutralized with a saturated sodium bicarbonate aqueous solution as needed). The resulting organic phase was directly subjected to purification by silica gel column chromatography (hexane/ethyl acetate or methylene chloride/methanol) to give 10.2 mg (27% yield) of the title compound as an orange powder with the following properties.

Aufarbeitung

  1. customIn a 20 mL reaction vessel
  2. stirringAfter the mixture was stirred at the same temperature for 1 hour
  3. stirringthe mixture was further stirred for 1 hour
  4. stirringthe mixture was stirred for 5 minutes to 1 hour (further, the mixture
  5. customThe resulting organic phase was directly subjected to purification by silica gel column chromatography (hexane/ethyl acetate or methylene chloride/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-effc935c0cbc4c57ab7221edeca15794
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399635B2

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