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

HRID 600132ノート

反応式

HRID 600132 の反応式
[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]

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 114323181,2,3,4,5,6,7,8-octapropyl-9,10-dihydroanthraceneHCID 178418339Butyllithium

生成物 1

HCID 114550891,2,3,4,5,6,7,8-octapropylanthracene収率 98%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  1. temperatureThe reaction solution was cooled to room temperature

出典と根拠

ORDレコード
ord-8d351671d206428789a2c987a1829422
出典データセット
uspto-grants-2011_03
特許番号
US07901594B2

反応ノート

読み込み中…