Ethylene Glycol → 3-[3-(1,3-Dioxolan-2-yl)phenoxy]propanamine

HRID 325680ノート

反応式

HRID 325680 の反応式
[CH:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][N:10]1C(=O)C2C(=CC=CC=2)C1=O)=[O:2].[CH2:24](O)[CH2:25][OH:26]>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:26]1[CH2:25][CH2:24][O:2][CH:1]1[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][NH2:10]

参加物

5

反応物 2

HCID 174Ethylene GlycolHCID 128106403-(3-(1,3-Dioxoisoindolin-2-yl)propoxy)benzaldehyde

生成物 1

HCID 127974473-[3-(1,3-Dioxolan-2-yl)phenoxy]propanamine収率 85%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 241Benzene溶媒

実験手順

A solution of 2-[3-(3-formylphenoxy)propyl]-1H-isoindole-1,3-(2H)-dione (90 g) and p-toluenesulphonic acid, monohydrate (200 mg) in benzene (900 ml) and ethane-1,2-diol (25 g) was heated under reflux using a Dean-Stark separator for 8 h. The cooled solution was washed successively with sodium carbonate solution, water, sodium chloride solution, and evaporated in vacuo. The resulting oil was dissolved in tetrahydrofuran (1 liter) and stirred with hydrazine hydrate (50 ml) at room temperature for 24 hr. The mixture was diluted with ether and filtered. The filtrate was distilled to give the title compound as a colourless oil (55.2 g) b.p. 134°-6° (0.7 mm). TLC silica; methanol:ammonia 80:1; Rf 0.4.

後処理

  1. temperatureunder reflux
  2. customfor 8 h
  3. washThe cooled solution was washed successively with sodium carbonate solution, water, sodium chloride solution
  4. customevaporated in vacuo
  5. dissolutionThe resulting oil was dissolved in tetrahydrofuran (1 liter)
  6. additionThe mixture was diluted with ether
  7. filtrationfiltered
  8. distillationThe filtrate was distilled

出典と根拠

ORDレコード
ord-def86e0895e9498a9071a9f3791cb42f
出典データセット
uspto-grants-1984_04
特許番号
US04442110

反応ノート

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