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

HRID 573109Notes

Reaction equation

HRID 573109 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.Cl>[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

7

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 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A mixture of dihydro-2H-pyran-4(3H)-one (10.0 g) and 2-chloroacetonitrile (7.5 g) in tert-butanol (10 mL) was treated with 1.0 N potassium tert-butoxide (100 mL) drop-wise over 20 minutes. The reaction mixture was stirred at room temperature for 16 hours. It was diluted with water (10 mL) and 10% aqueous HCl (20 mL). The reaction mixture was concentrated to one-third of its original volume, and extracted with diethyl ether four times. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel eluting with 20-40% ethyl acetate in hexanes.

Workup

  1. concentrationThe reaction mixture was concentrated to one-third of its original volume
  2. extractionextracted with diethyl ether four times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with flash column chromatography on silica gel eluting with 20-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-dcf9f48b762f45d49e25fcac855461bf
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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