Triethylamine → 2-Ethyl-4-(9-phenathryl)indene

HRID 1260

反応式

HRID 1260 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[C:13]3[C:18]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[CH:25]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:4]1O)[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([C:3]1[CH2:4][C:5]2[C:10]([CH:11]=1)=[C:9]([C:12]1[C:13]3[C:18]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[CH:25]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:8]=[CH:7][CH:6]=2)[CH3:2]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 212219312-Ethyl-1-hydroxy-4-(9-phenanthryl)indane

生成物 1

HCID 180081962-Ethyl-4-(9-phenathryl)indene収率 83%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A 300-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 12.3 g (36.3 mmol) of 2-ethyl-1-hydroxy-4-(9-phenanthryl)indane, 19.7 ml (142 mmol) of triethylamine and 61.5 ml of methylene chloride. To the mixture was gradually dropwise added a solution containing 3.3 ml (42.6 mmol) of methansulfonyl chloride dissolved in 5 ml of methylene chloride under a nitrogen atmosphere at 0° C. After the addition was completed, the temperature was elevated to room temperature, and the reaction mixture was stirred for additional 4 hours. To the reaction mixture was added 80 ml of a saturated aqueous solution of sodium bicarbonate. The organic phase was separated, and the aqueous phase was extracted with 50 ml of methylene chloride two times. The combined organic phase was washed with water, 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, and hexane/ethyl acetate (100/3 parts by volume)) to give 9.61 g of the desired product (mixture of two isomers) as a pasty pale yellow-green liquid (yield: 83%).

後処理

  1. customA 300-ml three-necked round flask equipped with a stirring bar
  2. additionTo the mixture was gradually dropwise added a solution
  3. additionAfter the addition
  4. customwas elevated to room temperature
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with 50 ml of methylene chloride two times
  7. washThe combined organic phase was washed with water
  8. dry with materialby drying over anhydrous Na2SO4
  9. customThe solvent was evaporated under reduced pressure
  10. customThe residue was chromatographed on silica gel (eluting with hexane, and hexane/ethyl acetate (100/3 parts by volume))

出典と根拠

ORDレコード
ord-c816ac4ef7654d68886954c067ebcb25
出典データセット
uspto-grants-1998_03
特許番号
US05723640

関連ノート

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