Ethylene Glycol → HCID 58609535、化合物

HRID 502916

反応式

HRID 502916 の反応式
[Na].[CH2:2]([OH:5])[CH2:3][OH:4].[C:6]([O-:10])(=[O:9])[CH2:7][OH:8].[Na+:11].[Br:12][C:13]1[C:14](=[O:22])[CH:15]2[CH2:21][CH:18]([C:19]=1Br)[CH:17]=[CH:16]2.P([O-])(O)(O)=O.[Na+]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[C:6]([O-:10])(=[O:9])[CH2:7][OH:8].[Na+:11].[Br:12][CH:13]1[C:19]2([O:5][CH2:2][CH2:3][O:4]2)[CH:18]2[CH2:21][CH:15]([CH:16]=[CH:17]2)[C:14]1=[O:22]

参加物

9

反応物 5

HCID 174Ethylene GlycolHCID 517347Sodium GlycolateHCID 5360545Sodium2 回HCID 23672064Monosodium phosphateHCID 68464392HCID 68464392、化合物

生成物 2

HCID 517347Sodium GlycolateHCID 58609535HCID 58609535、化合物収率 100%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 21226206Ethyl acetate hexane溶媒

実験手順

A sodium glycolate solution is prepared by stirring 124 mg (5.4 mmol) of metallic sodium into 2.7 ml (42.42 mmol) of anhydrous ethylene glycol at ambient temperature and, when the sodium has completely dissolved, 1.5 ml of tetrahydrofuran are added. To the resulting monosodium glycolate solution there is then added dropwise a solution of 1 g (3.6 mmol) of 3,4-dibromo-bicyclo[3.2.1]octa-3,6-dien-2-one (prepared according to Organic Lett. 4(12), 1997 (2002)) dissolved in 5 ml of tetrahydrofuran. The reaction mixture is then stirred at ambient temperature for 90 minutes with TLC monitoring (mobile phase hexane/ethyl acetate 4:1). The reaction mixture is then treated with 8 ml of 10% sodium dihydrogen phosphate solution and extracted with ethyl acetate (3×). The organic phase is washed with water to remove ethylene glycol, then dried and concentrated by evaporation. 930 mg (˜100%) of 3-bromo-4,4-ethylenedioxy-bicyclo[3.2.1]oct-6-en-2-one are obtained in the form of a white solid.

後処理

  1. extractionextracted with ethyl acetate (3×)
  2. washThe organic phase is washed with water
  3. customto remove ethylene glycol
  4. customdried
  5. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-305bc184b8f043d1932ca2e25f171f4c
出典データセット
uspto-grants-2010_08
特許番号
US07776888B2

関連ノート

読み込み中…