Methyl cyanoacetate → Methyl 4-cyanooxane-4-carboxylate

HRID 1186427Notes

Reaction equation

HRID 1186427 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].Br[CH2:9][CH2:10][O:11][CH2:12][CH2:13]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:3]1([C:4]([O:6][CH3:7])=[O:5])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2]

Participants

5

Reactant 3

HCID 7747Methyl cyanoacetateHCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) ether

Product 1

HCID 16726727Methyl 4-cyanooxane-4-carboxylateYield 61.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl cyanoacetate (2.50 mL, 28.3 mmol) and 2-bromoethyl ether (4.63 mL, 36.8 mol) were dissolved in acetone (50 ml). To this, potassium carbonate (9.78 g, 70.8 mmol) was added and the mixture was heated to reflux for 8 hours. The reaction mixture was filtered and the mother liquid was concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3) to give methyl 4-cyanotetrahydro-2H-pyran-4-carboxylate (2.93 g, yield: 61%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 8 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe mother liquid was concentrated
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-3183be388f634ac4a43b72a9a1053b9b
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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