Water → HCID 18786079, compound

HRID 1107849Notes

Reaction equation

HRID 1107849 reaction equation
[Br-].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:5]([NH:29][C:30](=O)[CH:31]=[CH2:32])[CH:4]=1.O.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1.C1COCC1>[CH:31]([C:30]1[NH:29][C:5]2[C:6]([CH:9]=1)=[CH:7][CH:8]=[C:3]([F:2])[CH:4]=2)=[CH2:32]

Participants

6

Reactant 3

HCID 962WaterHCID 18786088HCID 18786088, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18786079HCID 18786079, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 71.5 g (0.14 mol) sample of [[4-fluoro-2[(1-oxo-2-propenyl)amino]phenyl]-methyl]triphenylphosphonium bromide was suspended in 1.6 L of toluene and heated under reflux briefly with azeotropic removal of water. A 180 mL (0.18 mol) solution of 1M potassium t-butoxide in THF was added dropwise under Ar. The mixture was heated under reflux for one hour, cooled, washed with dilute HCl and filtered. The organic phase was washed with brine, dried (MgSO4) and concentrated. The residue was crystallized from methyl t-butyl ether (MTBE)/hexane. The precipitated triphenylphosphine oxide was collected and washed with MTBE. The combined filtrates were concentrated and flash chromatographed twice using EtOAc:hexane 1:10 as eluant. There was obtained 11.3 g (50%) of 2-ethenyl-6-fluoro-1H-indole: Cl-MS m/z=162 (M+H). 1H NMR (CDCl3) δ 8.1 (br s, 1H); 7.5 (m, 1H); 7.0 (d, 1H); 6.85 (m, 1H); 6.7 (m, 1H); 6.5 (s, 1H); 5.5 (d, 1H); 5.25 (d, 1H). ##STR19##

Workup

  1. temperatureheated
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for one hour
  4. temperaturecooled
  5. washwashed with dilute HCl
  6. filtrationfiltered
  7. washThe organic phase was washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was crystallized from methyl t-butyl ether (MTBE)/hexane
  11. customThe precipitated triphenylphosphine oxide was collected
  12. washwashed with MTBE
  13. concentrationThe combined filtrates were concentrated
  14. customflash chromatographed twice using EtOAc:hexane 1:10 as eluant

Sources & evidence

ORD record
ord-fe8be77827f14caabc395b64d1301990
Source dataset
uspto-grants-2000_05
Patent number
US06063803

Reaction notes

Loading…