Triethylamine → HCID 19382364, compound

HRID 2400046Notes

Reaction equation

HRID 2400046 reaction equation
[C:1]([C:7]1[O:8][CH:9]=[CH:10][C:11]=1[C:12]([OH:14])=O)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.ClC(OCC)=O.[N-:28]=[N+:29]=[N-:30].[Na+]>CC(C)=O.O>[C:1]([C:7]1[O:8][CH:9]=[CH:10][C:11]=1[C:12]([N:28]=[N+:29]=[N-:30])=[O:14])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 19382375HCID 19382375, compound

Product 1

HCID 19382364HCID 19382364, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2-Pivaloyl-3-furoic acid (1.96 g, 0.01 mol) was dissolved in acetone (40 ml) and the solution was stirred at 0° C. under nitrogen. Triethylamine (1.7 ml, 0.012 mol) was added, followed by ethyl chloroformate (1.24 ml, 0.013 mol) and the mixture was stirred for 11/2 hours. A solution of sodium azide (1.11 g, 0.017 mol) in water (4 ml) was added and the suspension was stirred for another 2 hours at 0° C. The solid was removed by filtration and the filtrate was diluted with water (25 ml). It was concentrated in vacuo to remove the acetone. The oil-water residue was extracted with ethyl acetate. The ethyl acetate extract was washed with saturated NaCl, dried over Na2SO4, filtered and concentrated to an amber oil (2.06 g) of 87% purity by HPLC.

Workup

  1. stirringthe mixture was stirred for 11/2 hours
  2. stirringthe suspension was stirred for another 2 hours at 0° C
  3. customThe solid was removed by filtration
  4. additionthe filtrate was diluted with water (25 ml)
  5. concentrationIt was concentrated in vacuo
  6. customto remove the acetone
  7. extractionThe oil-water residue was extracted with ethyl acetate
  8. extractionThe ethyl acetate extract
  9. washwas washed with saturated NaCl
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated to an amber oil (2.06 g) of 87% purity by HPLC

Sources & evidence

ORD record
ord-54709f26c0f94a4d820d586cd2d6e99e
Source dataset
uspto-grants-1995_09
Patent number
US05453424

Reaction notes

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