Triethylamine → 4-Ethyl-2-phenyl-1-indanone

HRID 585177

반응식

HRID 585177 반응식
C([CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:12]2C=CC=C[CH:13]=2)[CH:4]1[OH:18])C.C(N([CH2:24][CH3:25])CC)C.CS(Cl)(=O)=O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:12]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH2:11][CH:3]([C:25]1[CH:24]=[CH:5][CH:4]=[CH:3][CH:11]=1)[C:4]2=[O:18])[CH3:13]

참가 물질

6

반응물 3

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

생성물 1

HCID 223402224-Ethyl-2-phenyl-1-indanone수율 134.6%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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%)

후처리

  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)

출처 및 근거

ORD 기록
ord-5b4b98aff84c4fbe8e12924ea495bf97
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06930152B2

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