Triethylamine → HCID 6091949, compound

HRID 2389864Notes

Reaction equation

HRID 2389864 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[CH:7]/[C:8]([OH:10])=O.C(N(CC)CC)C.C1(P([N:32]=[N+:33]=[N-:34])(C2C=CC=CC=2)=O)C=CC=CC=1.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[CH:7]/[C:8]([N:32]=[N+:33]=[N-:34])=[O:10]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 6434022-Furanacrylic acid

Product 1

HCID 6091949HCID 6091949, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (2E)-3-(2-furyl)acrylic acid (660 g, 4.78 mol) and triethylamine (800 mL, 5.74 mol) in tetrahydrofuran (960 mL) was added diphenylphosphoryl azide (1.13 L, 5.26 mol) under ice-cooling. After stirring at room temperature for 4 hr, the reaction solution was poured into a mixture of ethyl acetate and saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with methanol to give the title compound (580 g, yield 74%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washThe residue was washed with methanol

Sources & evidence

ORD record
ord-2531c15df0324e35a8280b179ddb95b4
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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