Methyl cyanoacetate → HCID 54189837, compound

HRID 1378646Notes

Reaction equation

HRID 1378646 reaction equation
[CH3:1][O:2][C:3](=[O:7])[CH2:4][C:5]#[N:6].[CH2:8]([O:10][C:11](OCC)(OCC)[O:12][CH2:13][CH3:14])[CH3:9].C(OC(=O)C)(=O)C>>[CH3:1][O:2][C:3](=[O:7])[C:4]([C:5]#[N:6])=[C:11]([O:12][CH2:13][CH3:14])[O:10][CH2:8][CH3:9]

Participants

4

Reactant 3

HCID 7747Methyl cyanoacetateHCID 7918Acetic AnhydrideHCID 66213Tetraethyl orthocarbonate

Product 1

HCID 54189837HCID 54189837, compound

Conditions

Temperature
130 °C

Procedure

A reaction mixture consisting of methylcyanoacetate (5.0 ml, 57 mmol) and tetraethylorthocarbonate (17.99 ml, 86 mmol) in acetic anhydride (8.11 ml, 86 mmol) was heated at 130° C. for 5 hours, and then heated at 110° C. for 18 hours. The cooled reaction residue was extracted twice with 125 ml portions of hexane. A hexane-insoluble orange oil containing approximately 40% by weight of the desired compound (as established by NMR inspection) remained. This crude product was used in the next step without further purification. TLC Rf (silica gel plates, u.v. detection, ethyl acetate/hexane=15:85 in volume): 0.13.

Workup

  1. temperatureheated at 110° C. for 18 hours
  2. customThe cooled reaction residue
  3. extractionwas extracted twice with 125 ml portions of hexane
  4. additionA hexane-insoluble orange oil containing approximately 40% by weight of the desired compound (as established by NMR inspection)
  5. customThis crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-ae645c241a84447a9f12ea7100d837bc
Source dataset
uspto-grants-1997_09
Patent number
US05668145

Reaction notes

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