تفاعل #73490

معادلة التفاعل

hydrochloric acid

sodium sulphate

sodium borohydride

sodium hydroxide

4-methoxy-phenylmagnesium bromide

1,4-dioxa-spiro[4.5]decane-8-carbonitrile

→

desired product

C-(1,4-Dioxa-spiro[4.5]dec-8-yl)-C-(4-methoxy-phenyl)-methylamine

المذيبات

t-butyl methyl ether

THF

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةunder reflux for 16 hours
2. 2
   أخرىformed
3. 3
   أخرىThe precipitate was removed by filtration
4. 4
   غسيلwashed with THF

الإجراء التجريبي

Under argon, 4-methoxy-phenylmagnesium bromide (0.5M in THF, 24 mL, 12 mmol) was added to a solution of 1,4-dioxa-spiro[4.5]decane-8-carbonitrile (1.0 g, 6 mmol) in THF (100 mL). The mixture was stirred under reflux for 16 hours. The reaction mixture was then cooled to 0° C. Saturated sodium sulphate solution was added dropwise until no more precipitate formed. The precipitate was removed by filtration and washed with THF. The combined organic phases were stirred with sodium borohydride (452 mg, 12 mmol) overnight at 25° C. The reaction mixture was then diluted with t-butyl methyl ether (100 mL) and treated with 0.05M aqueous hydrochloric acid (three times with 100 mL). The combined aqueous phases were adjusted to alkaline pH with a 6M aqueous sodium hydroxide solution with cooling, before extraction with dichloromethane gave a solution of the desired product which was used directly in the next stage. Rt=0.74 min (Method 5). Detected mass: 278.2 (M+H+).

المصدر