Allyl bromide → HCID 178459151, compound

HRID 1029343Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][OH:19])[CH2:14][CH2:13]2)[CH2:8][CH2:7]1.[CH2:20](Br)[CH:21]=[CH2:22]>O1CCCC1>[CH2:20]([O:19][CH2:18][C@H:15]1[CH2:14][CH2:13][C@H:12]([C@H:9]2[CH2:10][CH2:11][C@H:6]([CH2:5][O:4][CH3:3])[CH2:7][CH2:8]2)[CH2:17][CH2:16]1)[CH:21]=[CH2:22]

Participants

Conditions

Temperature: 70 °C

Procedure

150 mg of sodium hydride (as a 50 percent suspension in oil) is suspended in 10 ml of absolute tetrahydrofuran and then treated dropwise at room temperature within 3 minutes with a solution of 0.5 g of [trans-4-[trans-4-(methoxymethyl)cyclohexyl]cyclohexyl]methanol in 8 ml of absolute tetrahydrofuran. The mixture is stirred for a further 5 minutes, then treated with 0.755 g of allyl bromide and stirred under reflux (bath temperature 70° C.) for 16 hours. Thereafter, the reaction mixture is partitioned in diethyl ether/water and extracted three times with diethyl ether. The organic phases are washed twice with water, dried over magnesium sulphate, filtered and evaporated. Chromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether (vol. 3:97) gives [trans-4-[trans-4-(methoxymethyl)cyclohexyl]cyclohexyl]methyl allyl ether.

Workup

stirringstirred
customThereafter, the reaction mixture is partitioned in diethyl ether/water
extractionextracted three times with diethyl ether
washThe organic phases are washed twice with water
dry with materialdried over magnesium sulphate
filtrationfiltered
customevaporated
customChromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether (vol. 3:97)

Sources & evidence

ORD record: ord-eecfe7d4e7054e1389329de96d52bd07
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05102578

Reaction notes

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