Methyl chloroglyoxylate → HCID 67258288, compound

HRID 1476673Notes

Reaction equation

HRID 1476673 reaction equation
[OH:1]/[N:2]=[C:3](\[NH2:9])/[CH2:4][O:5][CH2:6][CH2:7][CH3:8].Cl[C:11](=O)[C:12]([O:14][CH3:15])=[O:13]>C1COCC1>[CH2:6]([O:5][CH2:4][C:3]1[N:9]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[O:1][N:2]=1)[CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 79846Methyl chloroglyoxylateHCID 43248107HCID 43248107, compound

Product 1

HCID 67258288HCID 67258288, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1Z)—N′-hydroxy-2-propoxyethanimidamide (3.1 g) in absolute THF under Ar atmosphere is added CaH2 (1.09 g) and molecular sieves (4 A°). The mixture is stirred for 10 min and subsequently methyl chloro(oxo)acetate (3.16 g) is added and the reaction mixture is stirred for 3 h under reflux conditions. The mixture is filtered through celite and the filtrate is evaporated to dryness under vacuo. The resulting residue is purified by flash column chromatography (silica gel, eluent: cyclohexane/EtOAc, 3/2 (v/v)) to give the title compound as an oil.

Workup

  1. stirringthe reaction mixture is stirred for 3 h under reflux conditions
  2. filtrationThe mixture is filtered through celite
  3. customthe filtrate is evaporated to dryness under vacuo
  4. customThe resulting residue is purified by flash column chromatography (silica gel, eluent: cyclohexane/EtOAc, 3/2 (v/v))

Sources & evidence

ORD record
ord-4f38cd284cb240a788248338a5c64f9a
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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