Water → Cyclohexanone, 2-[(phenylmethoxy)methyl]-

HRID 1460605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1460605
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].Cl[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH2:16].[CH3:17][CH2:18]OCC>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[C:4]1([CH2:7][O:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=[O:16])[CH:18]=[CH:17][CH:1]=[CH:2][CH:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 3283Diethyl EtherHCID 137983Benzyl chloromethyl etherHCID 178418339Butyllithium

Produkt 1

HCID 10489011Cyclohexanone, 2-[(phenylmethoxy)methyl]-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 1-cyclohexenyloxytimethylsilane in dry tetrahydrofuran is treated with n-butyllithium (1.6M in hexane), 1.1 equivalents). After stirring 45 minutes the solution is cooled to 0° C. and a solution of zinc chloride (0.5 equivalents) in tetrahydrofuran is added dropwise. The mixture is stirred for 30 minutes followed by addition of choromethylbenzyl ether (1.2 equivalents) as a solution in tetrahydrofuran. After stirring for 6 hours, water is added. The organics are layered with ether, dried (MgSO4), concentrated in vacuo, then chromatographed to give the title compound.

Aufarbeitung

  1. stirringThe mixture is stirred for 30 minutes
  2. stirringAfter stirring for 6 hours
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-cf999f4eb96e49079bd22932521c0dcf
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05071853

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