Water → HCID 59648601, compound

HRID 1363294Notes

Reaction equation

HRID 1363294 reaction equation
[N:1]([C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:5][C:6]1[O:10][C:9](C(O)=O)=[CH:8][CH:7]=1)=[N+:2]=[N-:3].C([O-])(O)=O.[Na+].[B-](F)(F)(F)[F:25].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.O>CCOC(C)=O.CCCCCC>[N:1]([C:4](=[CH:5][C:6]1[O:10][C:9]([F:25])=[CH:8][CH:7]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2724933SelectfluorHCID 59683316HCID 59683316, compound

Product 1

HCID 59648601HCID 59648601, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 5-(2-azido-3-ethoxy-3-oxoprop-1-enyl)furan-2-carboxylic acid (0.50 g, 2.03 mmol) was added a mixture of NaHCO3 (0.34 g, 4.06 mmol) and Selectfluor® (1.08 g, 3.05 mmol), followed by water (4.0 mL), hexane (5.0 mL) and EtOAc (2.0 mL). The mixture was stirred at rt for 5 min. The organic layer was separated, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography (0 to 30% EtOAc in heptane over 20 min) yielded pure ethyl 2-azido-3-(5-fluorofuran-2-yl)prop-2-enoate as a reddish oil (0.20 g, 45%). 1H NMR (400 MHz, CD3OD) δ ppm 1.35 (t, J=7.15 Hz, 3H) 4.32 (q, J=7.16 Hz, 2H) 5.74 (dd, J=6.83, 3.66 Hz, 1H) 6.63 (s, 1H) 7.05 (t, J=3.59 Hz, 1H). 19F NMR (376 MHz, CD3OD) δ ppm −115.12 (dd, J=6.60, 3.30 Hz).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography (0 to 30% EtOAc in heptane over 20 min)

Sources & evidence

ORD record
ord-3a2e9491f9b9410585fd1fd6c436c117
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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