Diethyl Oxalate → HCID 54347591, compound

HRID 2296344Notes

Reaction equation

HRID 2296344 reaction equation
[CH2:1]([C:14]#[N:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[C:16](OCC)(=[O:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18].CC(C)([O-])C.[K+]>CN(C)C=O>[CH2:20]([O:19][C:17](=[O:18])[C:16](=[O:22])[CH:1]([C:14]#[N:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH3:21]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 64678TetradecanenitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 54347591HCID 54347591, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.5 Moles of n-tridecyl cyanide and 0.5 moles of diethyl oxalate are mixed in 1,000 ml of dimethylformamide. To this solution is added with ice cooling 0.52 moles of potassium t-butoxide. The mixture is allowed to stir overnight at room temperature. Following evaporation (rotary evaporator under vacuum) of most of the dimethylformamide the residue is mixed with 3 liters of diethyl ether followed by the addition of 1 liter water. The mixture is acidified with concentrated hydrochloric acid to a pH of 3 and then the ether phase is separated. After washing the ether with water and drying the ether over magnesium sulfate evaporation of the ether affords 3-cyano-2-oxopentadecanoic acid ethyl ester. Recrystallization from petroleum ether at 30°-60° C. provides pure material.

Workup

  1. customevaporation (rotary evaporator under vacuum) of most of the dimethylformamide the residue
  2. additionis mixed with 3 liters of diethyl ether
  3. additionfollowed by the addition of 1 liter water
  4. customthe ether phase is separated
  5. washAfter washing the ether with water
  6. dry with materialdrying the ether
  7. customover magnesium sulfate evaporation of the ether

Sources & evidence

ORD record
ord-35b8f197ac6e45c698b5aec2560e6202
Source dataset
uspto-grants-1984_01
Patent number
US04428959

Reaction notes

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