Reaktion #478386

Reaktionsgleichung

Dibal-H

tert-Butyldimethylsilyl chloride

ethyl 4-hydroxycyclohexanecarboxylate

imidazole

→

title compound

Ausbeute 91.7%

[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-methanol

Ausbeute 91.7%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenAfter washing with water (2×100 ml)
2. 2
   Trocknenthe organic phase was dried (MgSO4)
3. 3
   Sonstigeevaporated to dryness
4. 4
   workup.DISSOLUTIONThe residue was dissolved in dry THF (300 ml)
5. 5
   Temperaturcooled to −10° C
6. 6
   Sonstigewas kept at −10° C
7. 7
   workup.STIRRINGAfter stirring for 2 hrs the reaction
8. 8
   Sonstigewas quenched by slow addition of a saturated ammonium chloride solution (30 ml)
9. 9
   FiltrationThe resulting suspension was filtered
10. 10
    Einengenthe filtrate was concentrated in vacuo

Vorschrift

tert-Butyldimethylsilyl chloride (8.8 g, 58 mmol) was added to a solution of ethyl 4-hydroxycyclohexanecarboxylate (10 g, 58 mmol) and imidazole (4.3 g, 64 mmol) in DCM (300 ml), and the mixture was stirred overnight at 20° C. After washing with water (2×100 ml), the organic phase was dried (MgSO4) and evaporated to dryness. The residue was dissolved in dry THF (300 ml) and cooled to −10° C. Dibal-H (1.0 M in toluene, 174 ml, 174 mmol) was added dropwise over a period of 60 min, while the temperature was kept at −10° C. After stirring for 2 hrs the reaction was quenched by slow addition of a saturated ammonium chloride solution (30 ml). The resulting suspension was filtered, and the filtrate was concentrated in vacuo to give 13 g of the title compound as a mixture of two isomers. LC-MS (m/z): 245 (M+1).

Quelle