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Dimethylformamide → HCID 178500163、化合物

HRID 2389129
ノート
印刷プレビュー

反応式

HRID 2389129 の反応式
C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[C:12]([CH:16]1[CH2:21][CH2:20][CH:19]([O:22][C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([CH:33]([N+:35]([O-:37])=[O:36])[CH3:34])[CH:29]=3)[CH:24]=2)[CH2:18][CH2:17]1)([CH3:15])([CH3:14])[CH3:13].[C:38]([O:42][CH3:43])(=[O:41])[CH:39]=[CH2:40].[Cl-].[NH4+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OC(=O)C)C.O>[C:12]([C@H:16]1[CH2:21][CH2:20][C@H:19]([O:22][C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[CH:29]=[C:28]([C:33]([N+:35]([O-:37])=[O:36])([CH3:34])[CH2:40][CH2:39][C:38]([O:42][CH3:43])=[O:41])[CH:27]=[CH:26]3)[CH2:18][CH2:17]1)([CH3:13])([CH3:14])[CH3:15]
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

9

反応物 5

HCID 6228DimethylformamideHCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 866429012-(trans-4-Tert-butylcyclohexyloxy)-6-(1-nitroethyl)naphthalene

生成物 1

HCID 178500163HCID 178500163、化合物収率 72%

試薬・触媒・溶媒

3
HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

To a mixture of potassium carbonate (0.1783 g, 1.290 mmol), tetrabutylammonium hydrogen sulfate (0.005110 g, 0.01505 mmol) and N,N-dimethylformamide (3.00 mL, 38.7 mmol) was added 2-(4-tert-butyl-cyclohexyloxy)-6-(1-nitro-ethyl)-naphthalene (0.3821 g, 1.075 mmol). The mixture was stirred for 15 minutes, then methyl acrylate (0.1162 mL, 1.290 mmol) was added while maintaining the temperature at 20° C. (cool water bath). The mixture was stirred and allowed to reach room temperature. Stirring was continued (in slightly below room temperature water bath) for 2 hours and the reaction was monitored by HPLC. Ethylacetate and saturated aq. ammonium chloride were added and the layers were separated. The combined organic layer was dried over MgSO4, filtered, concentrated and purified by flash chromatography (0-20% EtOAc in hexanes) to give the title compound in 72% yield.

後処理

  1. stirringThe mixture was stirred
  2. customto reach room temperature
  3. stirringStirring
  4. customin slightly below room temperature
  5. customfor 2 hours
  6. customthe layers were separated
  7. dry with materialThe combined organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by flash chromatography (0-20% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-07c542c2d8df4d96a20073ec3039eb56
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08269043B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート