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

HRID 1660063Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-455b924ac59c4815b3c19d7dc801d626
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04306097

Reaction notes

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