Dibromomethane → 3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-dibromomethyl-4,5-dimethylcyclohexanol

HRID 1074491Notizen

Reaktionsgleichung

[Br:1][CH2:2][Br:3].[CH2:4]([O:11][C:12]1[CH:17]=[C:16]([C:18]([CH3:26])([CH3:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:15]=[CH:14][C:13]=1[CH:27]1[CH:32]([CH3:33])[CH:31]([CH3:34])[CH2:30][C:29](=[O:35])[CH2:28]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C1([N-]C2CCCCC2)CCCCC1.[Li+]>O1CCCC1.O.CCOCC>[CH2:4]([O:11][C:12]1[CH:17]=[C:16]([C:18]([CH3:25])([CH3:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:15]=[CH:14][C:13]=1[CH:27]1[CH:32]([CH3:33])[CH:31]([CH3:34])[CH2:30][C:29]([CH:2]([Br:3])[Br:1])([OH:35])[CH2:28]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a -78° C. solution of 17.4 g (0.10 mole) of dibromomethane and 21.7 g (0.050 mole) of 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4,5-dimethylcyclohexanone in 100 ml of tetrahydrofuran is added dropwise over a period of 2 hours a solution of lithium dicyclohexylamide (0.10 mole) in 100 ml of tetrahydrofuran. The reaction is stirred one hour longer at -78° C. and quenched by addition of 2 ml (0.11 mole) of water. The reaction is added to 300 ml ether and 200 ml water. The ether extract is dried over magnesium sulfate and evaporated. The crude product is purified via column chromatography on 500 g of silica gel eluted with ether-pentane to give pure 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-dibromomethyl-4,5-dimethylcyclohexanol.

Aufarbeitung

extractionThe ether extract
dry with materialis dried over magnesium sulfate
customevaporated
customThe crude product is purified via column chromatography on 500 g of silica gel
washeluted with ether-pentane

Quellen und Nachweise

ORD-Eintrag: ord-8f70a67810b340bcb5be7b0f5b31fabf
Quelldatensatz: uspto-grants-1983_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04391827

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