Tetrahydrofuran → 5-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(1-hydroxy-2-methoxyethyl)-1,3-thiazol-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1881877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881877
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:14](=[O:17])[CH:15]=[CH2:16])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[OH:25][CH:26]([C:30]1[S:34][C:33]([CH:35]=[O:36])=[N:32][CH:31]=1)[CH2:27][O:28][CH3:29].C(N(CC)CC)C.O1CCCC1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:14](=[O:17])[CH2:15][CH2:16][C:35]([C:33]3[S:34][C:30]([CH:26]([OH:25])[CH2:27][O:28][CH3:29])=[CH:31][N:32]=3)=[O:36])=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 593312584-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-oneHCID 593316105-(1-Hydroxy-2-methoxyethyl)-1,3-thiazole-2-carbaldehyde

Produkt 1

HCID 593314835-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(1-hydroxy-2-methoxyethyl)-1,3-thiazol-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dioneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

A mixture of 4-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (1.00 g), 5-(1-hydroxy-2-methoxyethyl)-1,3-thiazole-2-carbaldehyde (0.56 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (77 mg), triethylamine (0.16 mL), tetrahydrofuran (6 mL) and ethanol (6 mL) was stirred with heating under reflux for 2 hr. The reaction mixture was concentrated, the residue was subjected to basic silica gel column chromatography, and eluted with ethyl acetate, and the fraction was concentrated. The residue was subjected to silica gel column chromatography, and the title compound (1.46 g, yield 95%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (9:1, volume ratio). MS: 536 (MH+).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hr
  3. concentrationThe reaction mixture was concentrated
  4. washeluted with ethyl acetate
  5. concentrationthe fraction was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-0784138339054f078248840c08bd8b1b
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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