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Triethylamine → 2-ethyl-4-phenyl-1H-indene

HRID 1760054
ノート
印刷プレビュー

反応式

HRID 1760054 の反応式
[CH2:1]([CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]1O)[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([C:3]1[CH2:4][C:5]2[C:10]([CH:11]=1)=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:8]=[CH:7][CH:6]=2)[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 223402152-Ethyl-1-hydroxy-4-phenylindan

生成物 1

HCID 178307842-ethyl-4-phenyl-1H-indene収率 73%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane
溶媒
2 回

実験手順

To a 1-liter four-necked round flask (equipped with a stirrer, a dropping funnel and a thermometer) were fed 29.3 g (123.9 mmol) of 2-ethyl-1-hydroxy-4-phenylindane, 51.6 g (371.4 mmol) of triethylamine, 0.75 g (6.3 mmol) of 4-dimethylaminopyridine and 294 ml of methylene chloride. Then, a solution obtained by dissolving 19.2 ml (247.5 mmol) of methanesulfonyl chloride in 19.5 ml of methylene chloride was dropwise added slowly to the system while cooling with ice in a nitrogen atmosphere. After the addition was completed, the resulting mixture was reacted for another 3.5 hours at the same temperature. The reaction mixture was poured in 500 ml of ice water, then the organic phase was separated, and the aqueous phase was further extracted twice with 150 ml of methylene chloride. The whole organic phase was successively washed with a saturated NaHCO3 solution and a saturated salt solution, and dried with anhydrous Na2SO4. The solvent was distilled off under reduced pressure, and the residue was separated by silica gel chromatography (developed with hexane), to obtain 19.7 g of the aimed product (mixture of two kinds of isomers) as a light yellow liquid (yield: 73%)

後処理

  1. customTo a 1-liter four-necked round flask (equipped with a stirrer, a dropping funnel
  2. customThen, a solution obtained
  3. additionwas dropwise added slowly to the system
  4. temperaturewhile cooling with ice in a nitrogen atmosphere
  5. additionAfter the addition
  6. customthe resulting mixture was reacted for another 3.5 hours at the same temperature
  7. customthe organic phase was separated
  8. extractionthe aqueous phase was further extracted twice with 150 ml of methylene chloride
  9. washThe whole organic phase was successively washed with a saturated NaHCO3 solution
  10. dry with materiala saturated salt solution, and dried with anhydrous Na2SO4
  11. distillationThe solvent was distilled off under reduced pressure
  12. customthe residue was separated by silica gel chromatography (developed with hexane)

出典と根拠

ORDレコード
ord-d4d1c12e296e4cbab4f8c46ac58e8909
出典データセット
uspto-grants-2005_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06838522B2

反応ノート

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