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

HRID 574781Notes

Reaction equation

HRID 574781 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>[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

6

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 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent2×

Procedure

A mixture of tetrahydropyran-4-one (10 mL) and chloroacetonitrile (6.4 mL) in tert-butanol (10 mL) was stirred for 10 minutes. To this solution was added a solution of potassium tert-butoxide (12.11 g) in 200 mL of tert-butanol at room temperature over 40 minutes. The reaction mixture was stirred for 16 hours, diluted with water and quenched slowly with 1 N HCl. The solvent was partially removed by rotary evaporation. It was then extracted with ether (5×200 mL). The combined extracts was washed with brine, dried over MgSO4, filtered, and the filtrate was concentrated and purified by flash chromatography on silica with 3:7 to 1:1 ethyl acetate:hexanes to provide the title compound.

Workup

  1. stirringThe reaction mixture was stirred for 16 hours
  2. customquenched slowly with 1 N HCl
  3. customThe solvent was partially removed by rotary evaporation
  4. extractionIt was then extracted with ether (5×200 mL)
  5. washThe combined extracts was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. custompurified by flash chromatography on silica with 3:7 to 1:1 ethyl acetate

Sources & evidence

ORD record
ord-65fe9ea54af54fea8175445b78d201d1
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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