Tetrahydrofuran → HCID 58380602, Verbindung

HRID 1802881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802881
[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[CH:5][C:4]([CH:9]([CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:10](=[O:13])[CH:11]=[CH2:12])=[N:3]1.[O:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[O:27][CH2:28][C:29]1[S:33][C:32]([CH:34]=[O:35])=[N:31][CH:30]=1.C(N(CC)CC)C.O1CCCC1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[CH:5][C:4]([CH:9]([CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:10](=[O:13])[CH2:11][CH2:12][C:34]([C:32]2[S:33][C:29]([CH2:28][O:27][CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26][O:21]3)=[CH:30][N:31]=2)=[O:35])=[N:3]1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 58380621HCID 58380621, VerbindungHCID 593313055-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazole-2-carbaldehyde

Produkt 1

HCID 58380602HCID 58380602, VerbindungAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4-[1-methyl-5-(methylsulfanyl)-1H-pyrazol-3-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (0.60 g), 5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazole-2-carbaldehyde (0.48 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (54 mg), triethylamine (0.11 mL), tetrahydrofuran (6 mL) and ethanol (6 ml) was stirred with heating under reflux for 2 hr. The reaction mixture was concentrated, and the residue was subjected to basic silica gel column chromatography to give the title compound (0.65 g, yield 60%) as a yellow oil from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 522 (MH+).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hr
  3. concentrationThe reaction mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-e377f39b33e046a48040d1a0bfc8f4eb
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349886B2

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