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

HRID 600132노트

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HRID 600132 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8058Hexane용매

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온도
50 °C

실험 절차

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.

후처리

  1. temperatureThe reaction solution was cooled to room temperature

출처 및 근거

ORD 기록
ord-8d351671d206428789a2c987a1829422
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07901594B2

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