Nitrogen → 2-(2-Methyl-[1,3]dioxolan-2-yl)-oxazole-4-carboxylic acid ethyl ester

HRID 1044762Notes

Reaction equation

HRID 1044762 reaction equation
N#N.[CH2:3]([O:5][C:6]([C:8]1[N:9]=[C:10]([C:13](=[O:15])[CH3:14])[O:11][CH:12]=1)=[O:7])[CH3:4].COC([O:21][CH3:22])OC.[C:23]([O-])([O-])=O.[Na+].[Na+]>C(O)CO>[CH2:3]([O:5][C:6]([C:8]1[N:9]=[C:10]([C:13]2([CH3:14])[O:21][CH2:22][CH2:23][O:15]2)[O:11][CH:12]=1)=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 10340Sodium CarbonateHCID 66820192Ethyl 2-acetyloxazole-4-carboxylate

Product 1

HCID 668199002-(2-Methyl-[1,3]dioxolan-2-yl)-oxazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
95 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-acetyl-oxazole-4-carboxylic acid ethyl ester (7.0 g, 38.0 mmol) in ethylene glycol (42.7 mL) was treated with trimethylorthoformate (10.5 mL, 96.0 mmol) followed by LiBF4 (0.73 g, 8.0 mmol). The reaction mixture was heated at 95° C. until completion of the reaction. Aq. 0.5 M Na2CO3 was added and the mixture was extracted with Et2O. The org. layer was washed with aq. 0.5 M Na2CO3 (2×), dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 01: tR=0.76 min; [M+H]+=227.99.

Workup

  1. extractionthe mixture was extracted with Et2O
  2. washlayer was washed with aq. 0.5 M Na2CO3 (2×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-aeb10fd890e44974be64d3c572474ce5
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

Loading…