Triethylamine → HCID 58998478, compound

HRID 1852226Notes

Reaction equation

HRID 1852226 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10](O)=[O:11])=[CH:4][C:3]=1[O:13][CH3:14].C(N(CC)CC)C.C1C=CC(P([N:36]=[N+:37]=[N-:38])(C2C=CC=CC=2)=O)=CC=1>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:36]=[N+:37]=[N-:38])=[O:11])=[CH:4][C:3]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 218898501081765-44-7

Product 1

HCID 58998478HCID 58998478, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of (E)-3-(4-fluoro-3-methoxyphenyl)acrylic acid (5 g, 25.5 mmol) in benzene (30 ml) was added triethylamine (5.16 g, 51 mmol) followed by DPPA (7.01 g, 25.5 mmol) at room temperature. The reaction mass was stirred at the same temperature for 18 h. The solvent was evaporated under reduced pressure and the residue was diluted with water and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to get crude compound. The crude compound was purified by conventional column chromatography (Silica gel, 60-120 mesh) using 10% ethyl acetate in pet ether as mobile phase to get the desire compound as white solid (4 g, 71%). 1H NMR (400 MHz, CDCl3): δ ppm 7.70-7.66 (d, J=16 Hz, 1H), 7.12-7.07 (m, 3H), 6.35-6.31 (d, J=16 Hz, 1H), 3.92 (s, 3H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto get crude compound
  8. customThe crude compound was purified by conventional column chromatography (Silica gel, 60-120 mesh)

Sources & evidence

ORD record
ord-21cacee41fae443e8addd988851542a0
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

Loading…