Epichlorohydrin → {4-[(Oxiran-2-yl)methoxy]-1H-indol-6-yl}methanol

HRID 261804ノート

反応式

HRID 261804 の反応式
[OH:1][C:2]1[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH2:13]([CH:15]1[O:17][CH2:16]1)Cl.C[O-].[Na+]>>[O:17]1[CH2:16][CH:15]1[CH2:13][O:1][C:2]1[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

参加物

4

反応物 3

HCID 7835EpichlorohydrinHCID 10942334Sodium MethoxideHCID 233355196-(Hydroxymethyl)-1H-indol-4-ol

生成物 1

HCID 23335534{4-[(Oxiran-2-yl)methoxy]-1H-indol-6-yl}methanol

実験手順

3.3 g. of the 4-hydroxy-6-hydroxymethyl-indole thus prepared were dissolved in 30 ml. epichlorohydrin. To this solution were added dropwise, while stirring at ambient temperature, over the course of 1 hour, 20 ml. 2 N sodium methylate solution. After about 5 hours, the starting material had reacted. The solution was evaporated in a vacuum and the residue was mixed with water, as well as with a mixture of diethyl ether and ethyl acetate. The organic phase was shaken out several times with water, subsequently dried, treated with active charcoal and evaporated. The crude 4-(2,3-epoxypropoxy)-6-hydroxymethyl-indole thus obtained (about 5 g. of a brownish oil) contains, as by-product, some 4-(2-hydroxy-3-chloropropoxy)-6-hydroxymethyl-indole but was further used without further purification.

後処理

  1. dissolutionwere dissolved in 30 ml
  2. additionTo this solution were added dropwise
  3. waitAfter about 5 hours
  4. customthe starting material had reacted
  5. customThe solution was evaporated in a vacuum
  6. additionthe residue was mixed with water
  7. additionas well as with a mixture of diethyl ether and ethyl acetate
  8. stirringThe organic phase was shaken out several times with water
  9. customsubsequently dried
  10. additiontreated with active charcoal
  11. customevaporated

出典と根拠

ORDレコード
ord-9b5c57b2d35444bfa9f2ac2ae61925e9
出典データセット
uspto-grants-1979_05
特許番号
US04152446

反応ノート

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