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

HRID 20385

Reaction equation

HRID 20385 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-carbonitrileYield 59.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

Dissolve tetrahydropyran-4-one (5.0 mL, 54.2 mmol) and chloroacetonitrile (3.4 mL, 53.5 mmol) in tert-butanol (1 mL) and add drop-wise a solution of potassium tert-butoxide (54 mL, 54 mmol, 1.0 M in tert-butanol) over 20 minutes. Stir for 16 hours, dilute with water and quench slowly with 1 N hydrochloric acid. Extract with diethyl ether (×3). Combine extracts and wash with saturated aqueous sodium chloride solution, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 1:1 ethyl acetate:hexanes) to give the desired compound as a light yellow oil (4.4 g, 59%).

Workup

  1. additionadd
  2. customover 20 minutes
  3. customquench slowly with 1 N hydrochloric acid
  4. extractionExtract with diethyl ether (×3)
  5. washCombine extracts and wash with saturated aqueous sodium chloride solution
  6. dry with materialdry (magnesium sulfate)
  7. filtrationfilter
  8. concentrationconcentrate
  9. custompurify
  10. wash(silica gel chromatography, eluting with 0:100 to 1:1 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-3c8048ba8345462682c89c2f674e7eb4
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Linked notes

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