Water → 2-i-Butyl-4-(1-naphthyl)indene

HRID 1585188

Reaktionsgleichung

Reaktionsgleichung von HRID 1585188
[CH2:1]([C:5]1[CH:6](O)[C:7]2[C:12]([CH:13]=1)=[C:11]([C:14]1[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=1)[CH:10]=[CH:9][CH:8]=2)[CH:2]([CH3:4])[CH3:3].C(N(CC)CC)C.CS(Cl)(=O)=O.O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([C:5]1[CH2:6][C:7]2[C:12]([CH:13]=1)=[C:11]([C:14]1[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=1)[CH:10]=[CH:9][CH:8]=2)[CH:2]([CH3:4])[CH3:3]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 212219232-i-Butyl-1-hydroxy-4-(1-naphthyl)indene

Produkt 1

HCID 178438022-i-Butyl-4-(1-naphthyl)indeneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A 200-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 4.54 g (14.4 mmol) of 2-i-butyl-1-hydroxy-4-(1-naphthyl)indene, 5.13 g (50.8 mmol) of triethylamine, 0.10 g (0.82 mmol) of 4-dimethylaminopyridine and 57.7 ml of methylene chloride. To the mixture was added dropwise a solution containing 3.87 ml (33.8 mmol) of methanesulfonyl chloride dissolved in 7.7 ml of methylene chloride under a nitrogen atmosphere while cooling with ice bath. After the addition was completed, the temperature was elevated to room temperature and the mixture was further stirred for 3 hours. The reaction mixture was poured onto 100 ml of water. Thereafter, the organic phase was separated, and the aqueous phase was extracted with 50 ml of methylene chloride. The extracted organic phases were combined and washed with a saturated NaCl aq., followed by dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure. The residue was separated and purified with silica gel chromatography (eluting with hexane/ethyl acetate (20/1 parts by volume)) to obtain 3.98 g of the desired product (mixture of two isomers) as a pale yellow pasty liquid (yield: 93%).

Aufarbeitung

  1. customA 200-ml three-necked round flask equipped with a stirring bar
  2. additionTo the mixture was added dropwise a solution
  3. temperaturewhile cooling with ice bath
  4. additionAfter the addition
  5. customwas elevated to room temperature
  6. customThereafter, the organic phase was separated
  7. extractionthe aqueous phase was extracted with 50 ml of methylene chloride
  8. washwashed with a saturated NaCl aq.
  9. dry with materialby dried over anhydrous Na2SO4
  10. customThe solvent was evaporated under reduced pressure
  11. customThe residue was separated
  12. custompurified with silica gel chromatography (eluting with hexane/ethyl acetate (20/1 parts by volume))

Quellen und Nachweise

ORD-Eintrag
ord-fa63d074dc1d429da3e3d61b855e8a18
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05936053

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