Triethylamine → 2-ethyl-4-phenyl-1H-indene

HRID 1760054

Reaktionsgleichung

Reaktionsgleichung von HRID 1760054
[CH2:1]([CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]1O)[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([C:3]1[CH2:4][C:5]2[C:10]([CH:11]=1)=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:8]=[CH:7][CH:6]=2)[CH3:2]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 223402152-Ethyl-1-hydroxy-4-phenylindan

Produkt 1

HCID 178307842-ethyl-4-phenyl-1H-indeneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a 1-liter four-necked round flask (equipped with a stirrer, a dropping funnel and a thermometer) were fed 29.3 g (123.9 mmol) of 2-ethyl-1-hydroxy-4-phenylindane, 51.6 g (371.4 mmol) of triethylamine, 0.75 g (6.3 mmol) of 4-dimethylaminopyridine and 294 ml of methylene chloride. Then, a solution obtained by dissolving 19.2 ml (247.5 mmol) of methanesulfonyl chloride in 19.5 ml of methylene chloride was dropwise added slowly to the system while cooling with ice in a nitrogen atmosphere. After the addition was completed, the resulting mixture was reacted for another 3.5 hours at the same temperature. The reaction mixture was poured in 500 ml of ice water, then the organic phase was separated, and the aqueous phase was further extracted twice with 150 ml of methylene chloride. The whole organic phase was successively washed with a saturated NaHCO3 solution and a saturated salt solution, and dried with anhydrous Na2SO4. The solvent was distilled off under reduced pressure, and the residue was separated by silica gel chromatography (developed with hexane), to obtain 19.7 g of the aimed product (mixture of two kinds of isomers) as a light yellow liquid (yield: 73%)

Aufarbeitung

  1. customTo a 1-liter four-necked round flask (equipped with a stirrer, a dropping funnel
  2. customThen, a solution obtained
  3. additionwas dropwise added slowly to the system
  4. temperaturewhile cooling with ice in a nitrogen atmosphere
  5. additionAfter the addition
  6. customthe resulting mixture was reacted for another 3.5 hours at the same temperature
  7. customthe organic phase was separated
  8. extractionthe aqueous phase was further extracted twice with 150 ml of methylene chloride
  9. washThe whole organic phase was successively washed with a saturated NaHCO3 solution
  10. dry with materiala saturated salt solution, and dried with anhydrous Na2SO4
  11. distillationThe solvent was distilled off under reduced pressure
  12. customthe residue was separated by silica gel chromatography (developed with hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d4d1c12e296e4cbab4f8c46ac58e8909
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06838522B2

Verknüpfte Notizen

Wird geladen…