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Water → 3-(3,4-Dichlorophenyl)-3-butenol t-butyldimethylsilyl ether

HRID 1279338
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Reaktionsgleichung

Reaktionsgleichung von HRID 1279338
[CH3:1]C(C)([O-])C.[K+].[Si:7]([O:14][CH2:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)=O)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1C=CC=CC=1>[Si:7]([O:14][CH2:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)=[CH2:1])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 11198381HCID 11198381, VerbindungHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 108712633-(3,4-Dichlorophenyl)-3-butenol t-butyldimethylsilyl etherAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysator
HCID 241
Benzene
Lösungsmittel
2×

Versuchsvorschrift

215 g (0.60 mole) of methyltriphenylphosphonium bromide and 54 g (0.48 mole) of potassium t-butoxide were added to 2 liters of dried benzene, and the mixture was stirred for 9 hours at room temperature. At the end of this time, 40 g (0.12 mole) of 3-(3,4-dichlorophenyl)-3-oxo-1-propanol t-butyldimethylsilyl ether [prepared as described in step (b) above] were dissolved in 800 ml of benzene and the resulting solution was slowly added dropwise to the mixture over a period of 2.5 hours. 1 liter of water was then added to the reaction mixture, and the mixture was stirred for 30 minutes, whilst ice-cooling. The organic layer was separated, and then washed with water and with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using hexane as the eluent, to give 23.5 g of the title compound. The physicochemical properties of this product were the same as those of the product produced as described in Example 1(b).

Aufarbeitung

  1. additionthe resulting solution was slowly added dropwise to the mixture over a period of 2.5 hours
  2. stirringthe mixture was stirred for 30 minutes, whilst ice-
  3. temperaturecooling
  4. customThe organic layer was separated
  5. washwashed with water and with a saturated aqueous solution of sodium chloride
  6. dry with materialafter which it was dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d701013963cb4f528e9eb6ab269cdf4b
Quelldatensatz
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06448247B1

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