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1-Bromooctadecane → 1-Ethynyl-2-n-octadecylnaphthalene

HRID 2237072
ノート
印刷プレビュー

反応式

HRID 2237072 の反応式
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)#[CH:2].C([Li])CCC.CC(C)([O-])C.[K+].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>CCCCCC.O.O1CCCC1>[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH3:25])#[CH:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 82181-BromooctadecaneHCID 1233571-EthynylnaphthaleneHCID 23665647Potassium tert-butoxideHCID 178418339Butyllithium

生成物 1

HCID 866289541-Ethynyl-2-n-octadecylnaphthalene収率 19.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 8028
Tetrahydrofuran
溶媒
2 回
HCID 8058Hexane溶媒2 回

反応条件

温度
-90 °C

実験手順

To 20 mL of a tetrahydrofuran solution of 2.88 g of ethynylnaphthalene was added 25 mL of a 1.6 mol/L hexane solution of n-butyl lithium at −50° C. under a nitrogen atmosphere, and the mixture was cooled to −90° C., and then 12 mL of a tetrahydrofuran solution of 2.3 g of potassium tert-butoxide was added thereto. After stirring at −80° C. for 1 hour, the temperature was raised up to 5° C. At −70° C., 6.90 g of bromooctadecane was dropped to the resulting solution, and stirred overnight at 30° C. 100 mL of water was dropped to the resulting solution at 0° C., and hexane was added thereto to extract the generated compound. The hexane layer was washed with 30 mL of distilled water for 3 times, dried over anhydrous magnesium sulfate for 24 hours, followed by filtration, and the solvent was removed by evaporation. The resulting product was purified on a column by using hexane as a developing solvent, thereby 1.5 g of 1-ethynyl-2-n-octadecylnaphthalene was obtained. The obtained 1-ethynyl-2-n-decylnaphthalene was analyzed by 1H-NMR (270 MHz, CDCl3), and the NMR spectra showed peak at δ 8.3 (1H), 7.8 (2H), 7.5 (3H), 3.6 (1H), 3.0 (2H) 1.7 (2H), 1.3 (32H), 0.9 (3H).

後処理

  1. temperaturethe temperature was raised up to 5° C
  2. stirringstirred overnight at 30° C
  3. extractionto extract the generated compound
  4. washThe hexane layer was washed with 30 mL of distilled water for 3 times
  5. dry with materialdried over anhydrous magnesium sulfate for 24 hours
  6. filtrationfollowed by filtration
  7. customthe solvent was removed by evaporation
  8. customThe resulting product was purified on a column

出典と根拠

ORDレコード
ord-1030e1e405c84d3e866b51acbf30649f
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07715083B2

反応ノート

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