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

HRID 629618Notes

Reaction equation

HRID 629618 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 (7.55 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% HCl (20 mL). The reaction mixture was concentrated to one-third of its original volume, and extracted with diethyl ether four times.

Workup

  1. concentrationThe reaction mixture was concentrated to one-third of its original volume
  2. extractionextracted with diethyl ether four times

Sources & evidence

ORD record
ord-ea2e0bb3fe23402e8d3841a6c8f4f188
Source dataset
uspto-grants-2016_04
Patent number
US09315488B2

Reaction notes

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