Water → Spiro(2.6)nonan-4-one

HRID 2070610Notes

Reaction equation

HRID 2070610 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[C:7]1(=[O:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[I-].ClCC[S+](C)C.O>C(O)(C)(C)C>[CH2:1]1[C:8]2([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:7]2=[O:14])[CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 10400CycloheptanoneHCID 10912030(2-Chloroethyl)diMethylsulfoniuM iodideHCID 23665647Potassium tert-butoxide

Product 1

HCID 11062456Spiro(2.6)nonan-4-one

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a suspension of potassium tert-butoxide (3.48 g) in tert-butanol (32 mL) was added cycloheptanone (1.9 mL) while stirring under nitrogen atmosphere, followed by stirring the mixture at room temperature for 0.5 hour. Then, to the reaction mixture was added (2-chloroethyl)-dimethylsulfonium iodide (3.7 g) in eight portions over 1.6 hours, followed by stirring the mixture at room temperature for 16.5 hours. To the reaction mixture was added water, followed by extraction with diethyl ether. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (diethyl ether:hexane (volume ratio)=1:15) to give spiro[2.6]nonan-4-one (1.40 g).

Workup

  1. stirringby stirring the mixture at room temperature for 0.5 hour
  2. stirringby stirring the mixture at room temperature for 16.5 hours
  3. extractionfollowed by extraction with diethyl ether
  4. washThe organic layer was washed with saturated brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (diethyl ether:hexane (volume ratio)=1:15)

Sources & evidence

ORD record
ord-e7fa19e6946e4af1a5a544fedfab2380
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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