Methyl iodide → 1,2,3,4,5,6,7,8-octapropylanthracene

HRID 600132Notes

Reaction equation

[Li]CCCC.CN(C)CCN(C)C.[CH2:14]([C:17]1[C:30]2[CH2:29][C:28]3[C:23](=[C:24]([CH2:40][CH2:41][CH3:42])[C:25]([CH2:37][CH2:38][CH3:39])=[C:26]([CH2:34][CH2:35][CH3:36])[C:27]=3[CH2:31][CH2:32][CH3:33])[CH2:22][C:21]=2[C:20]([CH2:43][CH2:44][CH3:45])=[C:19]([CH2:46][CH2:47][CH3:48])[C:18]=1[CH2:49][CH2:50][CH3:51])[CH2:15][CH3:16].CI>CCCCCC>[CH2:43]([C:20]1[C:21]2[C:30](=[CH:29][C:28]3[C:23]([CH:22]=2)=[C:24]([CH2:40][CH2:41][CH3:42])[C:25]([CH2:37][CH2:38][CH3:39])=[C:26]([CH2:34][CH2:35][CH3:36])[C:27]=3[CH2:31][CH2:32][CH3:33])[C:17]([CH2:14][CH2:15][CH3:16])=[C:18]([CH2:49][CH2:50][CH3:51])[C:19]=1[CH2:46][CH2:47][CH3:48])[CH2:44][CH3:45]

Participants

Conditions

Temperature: 50 °C

Procedure

After 2.2 equivalents of n-BuLi and 2.2 equivalents of tetramethylethylenediamine were added to the hexane solution of 9,10-dihydro-1,2,3,4,5,6,7,8-octapropylanthracene at room temperature, the mixture was heated at 50° C. for 3 hours. The reaction solution was cooled to room temperature and 1.1 equivalent of methyl iodide was added thereto. Stirring for an hour produced the title compound in the NMR yield of 98%. The compound was treated with 3N hydrochloric acid, and washed with saturated sodium hydrogencarbonate aqueous solution and brine. The organic phase was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the pure title compound in the yield of 96%. In this case, purification by column chromatography, etc. was unnecessary.

Workup

temperatureThe reaction solution was cooled to room temperature

Sources & evidence

ORD record: ord-8d351671d206428789a2c987a1829422
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07901594B2

Reaction notes

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