Thiazole → Tert-butyl 4-hydroxy-4-(1,3-thiazol-2-yl)cyclohexanecarboxylate

HRID 1039931Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039931
C([Mg]Cl)(C)C.[Cl-].[Li+].[S:8]1[CH:12]=[CH:11][N:10]=[CH:9]1.[O:13]=[C:14]1[CH2:19][CH2:18][CH:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1>C1COCC1>[OH:13][C:14]1([C:9]2[S:8][CH:12]=[CH:11][N:10]=2)[CH2:15][CH2:16][CH:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]1

Komponenten

5

Edukt 3

HCID 9256ThiazoleHCID 14940589tert-Butyl 4-oxocyclohexane-1-carboxylateHCID 178461733HCID 178461733, Verbindung

Produkt 1

HCID 67257275Tert-butyl 4-hydroxy-4-(1,3-thiazol-2-yl)cyclohexanecarboxylateAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a flask containing TI-IF (82 mL) was added isopropylmagnesium chloride/lithium chloride (1.2 M in THF, 37.7 mL, 45 mmol). A solution of thiazole (3.5 g, 41 mmol) in THF (20 mL) was added slowly. The reaction was stirred for one hour. A solution of tert-butyl 4-oxocyclohexanecarboxylate (12.23 g, 62 mmol) in THF (20 mL) was added and the reaction was stirred for 3 hours. The reaction was then quenched slowly with saturated ammonium chloride and diluted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated. Flash chromatography was used for purification to yield tert-butyl 4-hydroxy-4-(1,3-thiazol-2-yl)cyclohexanecarboxylate (9.25 g, 33 mmol, 79% yield). MS ESI: [M+H]+ m/z 284.1.

Aufarbeitung

  1. additionTo a flask containing TI-IF (82 mL)
  2. stirringthe reaction was stirred for 3 hours
  3. customThe reaction was then quenched slowly with saturated ammonium chloride
  4. additiondiluted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customFlash chromatography was used for purification

Quellen und Nachweise

ORD-Eintrag
ord-678db9765ee340d4b0dc414f859646d3
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551984B2

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