Solketal → HCID 67254478, compound

HRID 1852328Notes

Reaction equation

HRID 1852328 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].[CH3:8][C:9]1([CH3:16])[O:13][CH:12](CO)[CH2:11][O:10]1>CN(C1C=CN=CC=1)C>[C:1]([CH2:3][C:4]([O:6][CH2:7][CH:11]1[CH2:12][O:13][C:9]([CH3:16])([CH3:8])[O:10]1)=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 7528SolketalHCID 7747Methyl cyanoacetate

Product 1

HCID 67254478HCID 67254478, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture of methyl cyanoacetate (1.3 ml, 15×10−3 mol), of solketal (1.25 ml, 10×10−3 mol) and of DMAP (2.7 mg, 0.03 equiv.) is heated at reflux with stirring for 30 hours in a reactor rendered inert with nitrogen. After cooling, the solvent is evaporated under vacuum and the brown oil obtained is chromatographed on a silica column (gradient of eluents: heptane/EtOAc from 90:10 to 80:20). 423 mg (yield: 23%) of the pure fractions of (2,2-dimethyl-1,3-dioxolan-4-yl)methyl cyanoacetate are thus obtained in the form of a yellow oil used as is in the following stage.

Workup

  1. temperatureat reflux
  2. temperatureAfter cooling
  3. customthe solvent is evaporated under vacuum
  4. customthe brown oil obtained
  5. customis chromatographed on a silica column (gradient of eluents: heptane/EtOAc from 90:10 to 80:20)

Sources & evidence

ORD record
ord-ebb0052f06d6412f905c044545d6ed17
Source dataset
uspto-grants-2015_02
Patent number
US08961941B2

Reaction notes

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