Diethyl Ether → Spiro[4.6]undecan-6-one

HRID 1337

Reaction equation

HRID 1337 reaction equation
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].CC[O:8][CH2:9][CH3:10].[CH3:11][CH2:12]OCC.[CH3:16][CH2:17][CH2:18]CC>>[CH2:3]1[C:1]2([CH2:4][CH2:18][CH2:17][CH2:16][CH2:10][C:9]2=[O:8])[CH2:2][CH2:12][CH2:11]1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 21877078Diethylether pentaneHCID 178418306HCID 178418306, compound

Product 1

HCID 10012276Spiro[4.6]undecan-6-one

Conditions

Temperature
-100 °C

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).

Workup

  1. temperaturemaintaining the temperature below -97° C
  2. temperatureThe reaction was warmed to -50° C. over two hours
  3. customthen quenched with a saturated solution of ammonium chloride
  4. extractionextracted with ethyl acetate (4×100 ml.)
  5. washwashed with brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a clear oil (

Sources & evidence

ORD record
ord-0d8ba9ae803d40f58c0f4e79b8f5ba5f
Source dataset
uspto-grants-1998_03
Patent number
US05723602

Linked notes

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