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

HRID 1779899
ノート
印刷プレビュー

反応式

HRID 1779899 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

A 300-ml four-necked round flask equipped with a stirring bar, a dropping funnel and a thermometer was charged with 9.78 g (41.3 mmol) of 2-ethyl-1-hydroxy-4-phenylindane, 17.2 ml (123.8 mmol) of triethylamine, 0.25 g (2.1 mmol) of 4-dimethylaminopyridine and 98 ml of methylene chloride. To the mixture was dropwise added a solution containing 6.4 ml (82.5 mmol) of methanesulfonyl chloride dissolved in 6.5 ml of methylene chloride under a nitrogen atmosphere at 0° C. After the addition was completed, the reaction mixture was stirred for 3.5 hours at this temperature. The reaction mixture was poured onto 250 ml of ice-water. Then, the organic phase was separated and the aqueous phase was further extracted with 50 ml of methylene chloride two times. The combined organic phase was washed with a saturated aqueous solution of NaHCO3, and then a saturated aqueous solution of sodium chloride, followed by drying over anhydrous Na2SO4. The solvent was evaporated under reduced pressure. The residue was chromatographed on silica gel (eluting with hexane) to obtain 6.56 g of the desired product as a pale yellow liquid (mixture of two kinds of isomers)(yield: 73%).

後処理

  1. customA 300-ml four-necked round flask equipped with a stirring bar, a dropping funnel
  2. additionTo the mixture was dropwise added a solution
  3. additionAfter the addition
  4. customThen, the organic phase was separated
  5. extractionthe aqueous phase was further extracted with 50 ml of methylene chloride two times
  6. washThe combined organic phase was washed with a saturated aqueous solution of NaHCO3
  7. dry with materialby drying over anhydrous Na2SO4
  8. customThe solvent was evaporated under reduced pressure
  9. customThe residue was chromatographed on silica gel (eluting with hexane)

出典と根拠

ORDレコード
ord-8acea2881b004c139e8aa694d95c6d31
出典データセット
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05629254

反応ノート

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