تفاعل #2350781

معادلة التفاعل

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

(bromomethyl)cyclopropane

KHMDS

→

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

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was cooled in an ice bath
2. 2
   أخرىquenched with sat. ammonium chloride solution
3. 3
   أخرىthe solvent evaporated
4. 4
   أخرىThe residue was partitioned between EtOAc (300 ml) and water (100 ml adjusted to pH 4 with 1 N HCl)
5. 5
   أخرىThe organic phase was separated
6. 6
   تجفيفdried over MgSO4
7. 7
   ترشيحfiltered
8. 8
   أخرىevaporated
9. 9
   أخرىto give an orange oil

الإجراء التجريبي

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).

المصدر