Reaction #1433

Reaction equation

t-Butyl lithium

ether

ether pentane

→

desired product

Spiro[4,6]undecan-6-one

Conditions

Workup

1. 1
   Temperaturemaintaining the temperature below -97° C
2. 2
   TemperatureThe reaction was warmed to -50° C. over two hours
3. 3
   Otherthen quenched with a saturated solution of ammonium chloride
4. 4
   Extractionextracted with ethyl acetate (4×100 ml.)
5. 5
   Washwashed with brine
6. 6
   Dryingdried (magnesium sulfate)
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated
9. 9
   Otherto give a clear oil (

Procedure

t-Butyl lithium (1.7M in pentane, 20.0 ml., 34 mmol.) was slowly added to ether (38 ml.) at -20° C. as the reaction was further cooled to -100° C. in a methanol/dry ice/liquid nitrogen bath. To this -100° C. solution was added the product from part (c) (5.0 g., 16.1 mmol.) in 2:1 ether/pentane (3 ml.) over 35 minutes, maintaining the temperature below -97° C. The reaction was warmed to -50° C. over two hours then quenched with a saturated solution of ammonium chloride, extracted with ethyl acetate (4×100 ml.), washed with brine, dried (magnesium sulfate), filtered and concentrated to give a clear oil (mixture of desired product and the iodo starting material).

Source