Reaktion #1952638

Reaktionsgleichung

1,4-dioxaspiro[4.5]decane-8-carbonitrile

(bromomethyl)cyclopropane

KHMDS

→

8-(Cyclopropylmethyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was cooled in an ice bath
2. 2
   Sonstigequenched with sat. ammonium chloride solution
3. 3
   Sonstigethe solvent evaporated
4. 4
   SonstigeThe residue was partitioned between EtOAc (300 ml) and water (100 ml adjusted to pH 4 with 1 N HCl)
5. 5
   SonstigeThe organic phase was separated
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated
9. 9
   Sonstigeto give an orange oil

Vorschrift

To a stirred solution of 1,4-dioxaspiro[4.5]decane-8-carbonitrile (20 g; 119.6136 mmol) and (bromomethyl)cyclopropane (17.76 g 12.6 ml; 131.57 mmol) in THF (100 ml) at −10° C. was added KHMDS (0.5M solution in toluene; 263.15 ml ; 131.57 mmol) dropwise and the solution allowed to warm to ambient temperature with stirring for 18 hours. The reaction was cooled in an ice bath and quenched with sat. ammonium chloride solution and the solvent evaporated. The residue was partitioned between EtOAc (300 ml) and water (100 ml adjusted to pH 4 with 1 N HCl). The organic phase was separated, dried over MgSO4, filtered and evaporated to give an orange oil. (21.0 g) 1H NMR δ (ppm)(CDCl3): 3.99-3.89 (4H, m), 2.08 (2H, d, J=13.5 Hz), 1.96-1.72 (9H, m), 0.96-0.82 (1H, m), 0.59-0.53 (2H, m), 0.17 (2H, q, J=5.1 Hz).

Quelle