Hydrochloric Acid → 5-(2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-cyclohexen-1-one

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Reaktionsgleichung

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[CH:24]1[CH2:29][C:28](=O)[CH:27]=[C:26]([O:31]C)[CH2:25]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>CCOCC>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:22])([CH3:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[CH:24]1[CH2:25][C:26](=[O:31])[CH:27]=[CH:28][CH2:29]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a 0° C. solution of the title compound of Example 31, 5-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-3-methoxy-2-cyclohexen-1-one (500 mg, 1.15 mmole), in ether (20 ml) was added lithium aluminum hydride (20 mg, 0.53 mmole). The reaction mixture was stirred for 30 minutes at 0° C., acidified with 1 N hydrochloric acid and stirred for 2 hours at room temperature. The ether phase was removed, washed successively with saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate and evaporated. The crude oil was purified via column chromatography on 100 g of silica gel eluted with 50% ether-pentane to yield 353 mg (76%) of the title compound as an oil.

Aufarbeitung

stirringstirred for 2 hours at room temperature
customThe ether phase was removed
washwashed successively with saturated sodium bicarbonate, saturated sodium chloride
dry with materialdried over magnesium sulfate
customevaporated
customThe crude oil was purified via column chromatography on 100 g of silica gel
washeluted with 50% ether-pentane

Quellen und Nachweise

ORD-Eintrag: ord-2434168f14e3441eb7a841b51034c6d0
Quelldatensatz: uspto-grants-1983_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04391827

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