Dimethylformamide → 1-Chloro-3,4-dihydronaphthalene-2-carboxaldehyde

HRID 330267

反応式

HRID 330267 の反応式
P(Cl)(Cl)([Cl:3])=O.CN([CH:9]=[O:10])C.[C:11]1(=O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1.C([O-])(=O)C.[Na+]>ClC=C(Cl)Cl>[Cl:3][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][C:12]=1[CH:9]=[O:10]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 107241-TetraloneHCID 24813Phosphorus oxychlorideHCID 517045Sodium Acetate

生成物 1

HCID 767521-Chloro-3,4-dihydronaphthalene-2-carboxaldehyde収率 94.7%

試薬・触媒・溶媒 1

HCID 6575Trichloroethylene溶媒2 回

反応条件

温度
60 °C

実験手順

Phosphorus oxychloride (25.82 mL, 0.277 mol) was added dropwise to a solution of trichloroethylene (62.5 mL) and DMF (25.48 mL, 0.329 mol) keeping the temperature between 5°-10° C. -Tetralone (40 g, 0.274 mol) in trichloroethylene (62.5 mL) was added dropwise. The reaction mixture was stirred at 60° C. for 3 hours and at room temperature overnight. An aqueous sodium acetate solution (100 g/300 mL H2O) was added dropwise while cooling in a water bath. The aqueous phase was extracted with ether (3×200 mL), dried (MgSO4) and concentrated to give an oil (50 g). 20 g of this crude oil was chromatographed on silica gel with 50% ethyl acetate/hexane to yield 9.95 g (50%) of pure product as a white solid, m.p. 37° C.

後処理

  1. custombetween 5°-10° C.
  2. additionwas added dropwise
  3. temperaturewhile cooling in a water bath
  4. extractionThe aqueous phase was extracted with ether (3×200 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-00231c375a0f43eabe0f89314b3c9f86
出典データセット
uspto-grants-1990_01
特許番号
US04895860

関連ノート

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