Water → 2-i-Butyl-4-(1-naphthyl)indene

HRID 2258075

反応式

HRID 2258075 の反応式
[CH2:1]([C:5]1[CH:6](O)[C:7]2[C:12]([CH:13]=1)=[C:11]([C:14]1[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=1)[CH:10]=[CH:9][CH:8]=2)[CH:2]([CH3:4])[CH3:3].C(N(CC)CC)C.CS(Cl)(=O)=O.O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([C:5]1[CH2:6][C:7]2[C:12]([CH:13]=1)=[C:11]([C:14]1[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=1)[CH:10]=[CH:9][CH:8]=2)[CH:2]([CH3:4])[CH3:3]

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 212219232-i-Butyl-1-hydroxy-4-(1-naphthyl)indene

生成物 1

HCID 178438022-i-Butyl-4-(1-naphthyl)indene収率 93%

試薬・触媒・溶媒 2

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

実験手順

A 200-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 4.54 g (14.4 mmol) of 2-i-butyl-1-hydroxy-4-(1-naphthyl)indene, 5.13 g (50.8 mmol) of triethylamine, 0.10 g (0.82 mmol) of 4-dimethylaminopyridine and 57.7 ml of methylene chloride. To the mixture was added dropwise a solution containing 3.87 ml (33.8 mmol) of methanesulfonyl chloride dissolved in 7.7 ml of methylene chloride under a nitrogen atmosphere while cooling with ice bath. After the addition was completed, the temperature was elevated to room temperature and the mixture was further stirred for 3 hours. The reaction mixture was poured onto 100 ml of water. Thereafter, the organic phase was separated, and the aqueous phase was extracted with 50 ml of methylene chloride. The extracted organic phases were combined and washed with a saturated NaCl aq., followed by dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure. The residue was separated and purified with silica gel chromatography (eluting with hexane/ethyl acetate (20/1 parts by volume)) to obtain 3.98 g of the desired product (mixture of two isomers) as a pale yellow pasty liquid (yield: 93%).

後処理

  1. customA 200-ml three-necked round flask equipped with a stirring bar
  2. additionTo the mixture was added dropwise a solution
  3. temperaturewhile cooling with ice bath
  4. additionAfter the addition
  5. customwas elevated to room temperature
  6. customThereafter, the organic phase was separated
  7. extractionthe aqueous phase was extracted with 50 ml of methylene chloride
  8. washwashed with a saturated NaCl aq.
  9. dry with materialby dried over anhydrous Na2SO4
  10. customThe solvent was evaporated under reduced pressure
  11. customThe residue was separated
  12. custompurified with silica gel chromatography (eluting with hexane/ethyl acetate (20/1 parts by volume))

出典と根拠

ORDレコード
ord-32fb3139ed1c4d17a9b8ca3a1cf3d8e3
出典データセット
uspto-grants-1997_08
特許番号
US05658997

関連ノート

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