Acetic acid, azido-, ethyl ester → HCID 86618339, compound

HRID 1713043Notes

Reaction equation

HRID 1713043 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[O:13][C:12]([CH:14]=O)=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:18]([O:20][C:21](=[O:26])[CH2:22][N:23]=[N+:24]=[N-:25])[CH3:19].C1CCN2C(=NCCC2)CC1>C(O)C>[CH2:18]([O:20][C:21](=[O:26])[C:22]([N:23]=[N+:24]=[N-:25])=[CH:14][C:12]1[O:13][C:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:17][CH:16]=2)=[CH:10][CH:11]=1)[CH3:19]

Participants

5

Reactant 3

HCID 69480Acetic acid, azido-, ethyl esterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 35900455-(4-nitrophenoxy)furan-2-carbaldehyde

Product 1

HCID 86618339HCID 86618339, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Absolute ethanol (20 ml) was added to 5-(4-nitro-phenoxy)-furan-2-carbaldehyde (275 mg, 1.18 mmol) and the mixture was heated to 70° C. until a limpid solution was obtained. Azido-acetic acid ethyl ester (1.827 grams, 14.2 mmol) and DBU (286.9 mg, 1.89 mmol) were then added and the mixture was heated at 70° C. for one and a half hours. The solvent was thereafter removed under reduced pressure and a solution of HCl 0.1 M (50 ml) and ethyl acetate (20 ml) were added. After separation of the phases the aqueous phase was extracted with ethyl acetate (2×20 ml), the combined organic phase was dried over Na2SO4 and the organic solvents were evaporated under reduced pressure. The crude product was purified by silica gel flash chromatography to give 148.5 mg of pure 2-azido-3-(5-(4-nitrophenoxy)-furan-2-yl)-acrylic acid ethyl ester (36.5% yield).

Workup

  1. customwas obtained
  2. temperaturethe mixture was heated at 70° C. for one and a half hours
  3. customThe solvent was thereafter removed under reduced pressure
  4. additiona solution of HCl 0.1 M (50 ml) and ethyl acetate (20 ml) were added
  5. customAfter separation of the phases the aqueous phase
  6. extractionwas extracted with ethyl acetate (2×20 ml)
  7. dry with materialthe combined organic phase was dried over Na2SO4
  8. customthe organic solvents were evaporated under reduced pressure
  9. customThe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-9280d0a616cd4c23aec22eb6e6ef97a9
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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