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

HRID 609519
ノート
印刷プレビュー

反応式

HRID 609519 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 72.1%

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 300-ml four-necked round flask (equipped with a stirrer tip, a dropping funnel and a thermometer) were introduced 9.78 g (41.3 mmol) of 2-ethyl-1-hydroxy-4-phenylindan, 17.2 ml (123.8 mmol) of triethylamine, 0.25 g (2.1 mmol) of 4-dimethylaminopyridine and 98 ml of methylene chloride, and then in a nitrogen atmosphere under ice cooling, a solution of 6.4 ml (82.5 mmol) of methanesulfonyl chloride in 6.5 ml of methylene chloride was dropwise added slowly. After the dropwise addition was completed, the reaction was performed for further 3.5 hours at the same temperature. The reaction mixture was poured into 250 ml of ice water, the organic phase was separated, and the aqueous phase was extracted twice with 50 ml of methylene chloride. The combined organic phases were washed with a saturated NaHCO3 aqueous solution and then with a saturated saline solution, followed by drying over anhydrous Na2SO4. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography using hexane to obtain 6.56 g of the aimed product (a mixture of isomers) as a light yellow liquid (yield: 73%). The properties of the product thus obtained are described below.

後処理

  1. customTo a 300-ml four-necked round flask (equipped with a stirrer tip, a dropping funnel
  2. additionAfter the dropwise addition
  3. customthe organic phase was separated
  4. extractionthe aqueous phase was extracted twice with 50 ml of methylene chloride
  5. washThe combined organic phases were washed with a saturated NaHCO3 aqueous solution
  6. dry with materialby drying over anhydrous Na2SO4
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-4daad2cc5fc248529c67dc5501cbe798
出典データセット
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05998039

反応ノート

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