Reaction #73479

Reaction equation

NaOH

phenylmagnesium bromide

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

methyl lithium

→

pale yellow oil

1-(1,4-Dioxa-spiro[4.5]dec-8-yl)-1-phenyl-ethylamine

Solvents

—

ice water

diethyl ether

diethyl ether

Conditions

Workup

1. 1
   workup.STIRRINGAfter stirring for 5 min
2. 2
   Temperaturethe reaction was heated
3. 3
   Temperatureunder reflux for 10 hours
4. 4
   ExtractionThe mixture was extracted with t-butyl methyl ether
5. 5
   Dryingdried over sodium sulphate
6. 6
   FiltrationAfter filtration the organic phase
7. 7
   Otherwas evaporated

Procedure

Under argon, phenylmagnesium bromide (3M) in diethyl ether (6.7 mL, 20 mmol) was added to a solution of 1,4-dioxa-spiro[4.5]decane-8-carbonitrile (3.34 g, 20 mmol) in diethyl ether (60 mL). The mixture was stirred for 30 minutes. Titanium (IV) isopropoxide (5.7 g, 20 mmol) was then added. After stirring for 5 min, methyl lithium (1.6 M in diethyl ether, 31.2 mL, 50 mmol) was added and the reaction was heated under reflux for 10 hours. After cooling in ice/water the brown mixture was treated cautiously with 2M NaOH solution (30 mL) dropwise (exothermic). The mixture was extracted with t-butyl methyl ether and dried over sodium sulphate. After filtration the organic phase was evaporated to give 5 g of a pale yellow oil, which was used in the next step without further purification. Rt=2.10 min (Method 2). Detected mass: 261.2 (M+H+).

Source