Reaction #931191

Reaction equation

1,4-Dioxa-spiro[4,5]decan-8-one

tosyl-methyl isocyanate

tBuOK

→

solid

Yield 67.7%

1,4-Dioxa-spiro[4,5]decane-8-carbonitrile

Yield 67.7%

Solvents

dimethylformamide

water

Conditions

Workup

1. 1
   Extractionextracted with diethyl ether
2. 2
   WashThe combined extracts were washed with water and brine
3. 3
   Dryingdried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated to a solid which
6. 6
   Otherwas purified via flash chromatography on silica using 30% ethyl acetate/hexane as eluent

Procedure

To a solution of 1,4-Dioxa-spiro[4,5]decan-8-one (2.0 grams, 12.8 mmole) and tosyl-methyl isocyanate (5.0 grams, 25.6 mmole) in dimethylformamide (25 ml) at 0° C. was added 1.0 M tBuOK in tButanol (25.6 ml) and stirred at 0° C. for 1 hour and room temperature over night. The mixture was diluted with water and extracted with diethyl ether. The combined extracts were washed with water and brine, dried over MgSO4, filtered, and concentrated to a solid which was purified via flash chromatography on silica using 30% ethyl acetate/hexane as eluent to give a solid (1.45 g). MW 167.209; MS (m/e) 168 (M++1).

Source