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

HRID 1489315

Reaktionsgleichung

Reaktionsgleichung von HRID 1489315
[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 300-ml four-necked round flask (equipped with stirrer chip, dropping funnel and thermometer) were introduced 9.78 g (41.3 mmol) of the 2-ethyl-1-hydroxy-4-phenylindan obtained above, 17.2 ml (123.8 mmol) of triethylamine, 0.25 g (2.1 mmol) of 4-dimethylaminopyridine and 98 ml of methylene chloride. In a nitrogen atmosphere under ice cooling, to the flask was dropwise added slowly a solution obtained by dissolving 6.4 ml (82.5 mmol) of methanesulfonyl chloride in 6.5 ml of methylene chloride. After the dropping was completed, the reaction was further performed for 3.5 hours. After the reaction mixture was poured into 250 ml of ice water, the organic phase was separated, and the aqueous phase was extracted twice with 50 ml of methylene chloride, followed by mixing the organic phases together. The whole organic phase was washed with a saturated NaHCO3 aqueous solution and then washed with a saturated saline solution, followed by drying with anhydrous Na2SO4. The solvent was distilled off under reduced pressure, and the residue was separated and purified by silica gel chromatography (developed with hexane) to obtain 6.56 g of the aimed product (mixture of two kinds of isomers) as a light yellow liquid (yield: 73%) The properties of the product thus obtained are described below.

Aufarbeitung

  1. customTo a 300-ml four-necked round flask (equipped with stirrer chip, dropping funnel and thermometer)
  2. additionIn a nitrogen atmosphere under ice cooling, to the flask was dropwise added slowly a solution
  3. customobtained
  4. customthe organic phase was separated
  5. extractionthe aqueous phase was extracted twice with 50 ml of methylene chloride
  6. additionby mixing the organic phases together
  7. washThe whole organic phase was washed with a saturated NaHCO3 aqueous solution
  8. washwashed with a saturated saline solution
  9. dry with materialby drying with anhydrous Na2SO4
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe residue was separated
  12. custompurified by silica gel chromatography (developed with hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a879a9169dde4265b8ed4a63d456505c
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05677408

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