Chloroacetonitrile → 1,6-Dioxaspiro[2.5]octane-2-carbonitrile

HRID 1095389Notes

Reaction equation

HRID 1095389 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.Cl[CH2:9][C:10]#[N:11].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[O:7]1[C:4]2([CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:9]1[C:10]#[N:11]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 121599Tetrahydro-4H-pyran-4-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 214379031,6-Dioxaspiro[2.5]octane-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a mixture of tetrahydro-4H-pyran-4-one (5.0 g, 50 mmol) and chloroacetonitrile (3.8 g, 50 mmol) was dropwise added a solution of potassium tert-butoxide in tert-butanol (1.0 M, 50 mL). The reaction mixture was stirred overnight and quenched with water (100 mL). The whole was extracted with ethyl acetate (200 mL). The organic layer was washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo to afford the titled compound. (5.65 g)

Workup

  1. customquenched with water (100 mL)
  2. extractionThe whole was extracted with ethyl acetate (200 mL)
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3eabbf032c23491d9b621f417e5ee99e
Source dataset
uspto-grants-2012_03
Patent number
US08138177B2

Reaction notes

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