Water → 1,4-Dioxaspiro[4.5]decane-8-carbonitrile

HRID 1748506Notes

Reaction equation

HRID 1748506 reaction equation
C1(C)C=CC(S([CH2:10][N+:11]#[C-])(=O)=O)=CC=1.[CH2:14]1[O:24][C:17]2([CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]2)[O:16][CH2:15]1.CC(C)([O-])C.[K+].O>COCCOC.C(O)C>[O:16]1[C:17]2([CH2:22][CH2:21][CH:20]([C:10]#[N:11])[CH2:19][CH2:18]2)[O:24][CH2:14][CH2:15]1

Participants

7

Reactant 4

HCID 962WaterHCID 161915Tosylmethyl isocyanideHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 111164331,4-Dioxaspiro[4.5]decane-8-carbonitrileYield 72%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

p-Toluenesulfonylmethylisocyanide (27.0 g) was added at room temperature to a solution of 1,4-cyclohexanedione monoethyleneketal (16.6 g) in 1,2-dimethoxyethane (133 ml) and ethanol (13 ml). Then, potassium tert-butoxide was added under ice cooling over an hour, and stirred at room temperature for three hours. After completion of the reaction, water was added and extracted with ethyl acetate three times. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1,4-dioxaspiro[4,5]decane-8-carbonitrile (12.8 g) as a colorless oil.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate three times
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-41cda5b126f94b108dbf6a875ef39b3d
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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