Thiazole → 1-{[Tert-butyl(dimethyl)silyl]oxy}-2-(1,3-thiazol-2-yl)propan-2-ol

HRID 410448

Reaktionsgleichung

Reaktionsgleichung von HRID 410448
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Si:6]([O:13][CH2:14][C:15](=[O:17])[CH3:16])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]>C1COCC1>[Si:6]([O:13][CH2:14][C:15]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)([OH:17])[CH3:16])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Komponenten

4

Edukt 2

HCID 9256ThiazoleHCID 41249691-(tert-Butyldimethylsilyloxy)-2-propanone

Produkt 1

HCID 674295761-{[Tert-butyl(dimethyl)silyl]oxy}-2-(1,3-thiazol-2-yl)propan-2-olAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Isopropylmagnesium chloride-lithium chloride complex (2.98 ml, 3.88 mmol) was dissolved in THF (4 mL). Thiazole (0.252 ml, 3.52 mmol) in THF (2 mL) was added slowly. After 1 h, 1-(tert-butyldimethylsilyloxy)-2-propanone (0.816 ml, 4.23 mmol) in THF (2 mL) was added and the reaction was stirred for 3 h at room temperature. The reaction was quenched with saturated ammonium chloride and extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo. Purification via silica gel column chromatography (5%-10% EtOAc:hexanes) afforded 1-{[tert-butyl(dimethyl)silyl]oxy}-2-(1,3-thiazol-2-yl)propan-2-ol (383 mg, 40%) as a yellow oil. MS EST: [M+H]+ m/z 274.

Aufarbeitung

  1. customThe reaction was quenched with saturated ammonium chloride
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via silica gel column chromatography (5%-10% EtOAc:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-dcef9512cdb34819bce53f801b516908
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759366B2

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