Ethyl formate → HCID 86759857, compound

HRID 967009Notes

Reaction equation

HRID 967009 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:13]([O-:15])=O)CO2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N-:16]=[N+:17]=[N-:18].[Na+].[CH:20]([O:22][CH2:23][CH3:24])=[O:21]>CCO.O.CCOC(C)=O>[N:16]([CH:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH:13]([OH:15])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N+:17]=[N-:18]

Participants

6

Reactant 3

HCID 8025Ethyl formateHCID 33557Sodium AzideHCID 86759858HCID 86759858, compound

Product 1

HCID 86759857HCID 86759857, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 19096565Water ethanolSolvent

Procedure

A mixture of ethyl (2RS,3RS)-3-(4-nitrophenyl-2-oxirane carboxylate [prepared by the method of Moyna, G., Williams, H. J., Scott, A. I., Synth. Commun, (1996) 26, 2235-9] (2.5 g, 10.5 mmol) sodium azide (3.4 g, 52.5 mmol), ethyl formate (10 ml) in EtOH/water (8:1, 50 ml) was heated at 50° overnight. The mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4) and evaporated in vacuo. Column chromatography (SiO2; MeOH/DCM, 1:99) gave the title compound as a yellow oil (2.34 g) (less polar regioisomer). δH (CDCl3) 8.24 (2H, d, J 8.8 Hz, ArH), 7.55 (2H, d, J 8.9 Hz, ArH), 5.02 (1H, d, J 3.7 Hz, CHN3), 4.57 (1H, dd, J 5.3, 3.7 Hz, CHOH), 4.25-4.14 (2H, m, CO2CH2), 3.15 (1H, d, J 5.5 Hz, OH), 1.21 (3H, t, J 7.2 Hz, CO2CH2CH3). m/z (ES+, 70V) 253 (M+−N2).

Workup

  1. customprepared by the method of Moyna, G
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-3f41e5fbcc55472f93e19c8f5813b949
Source dataset
uspto-grants-2005_10
Patent number
US06953798B1

Reaction notes

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