Hydrochloric Acid → [5-(5-Methyl-tetrazol-1-yl)-benzofuran-7-yl]-methanol

HRID 1584777ノート

反応式

HRID 1584777 の反応式
[OH:1][CH2:2][C:3]1[C:11]2[O:10][CH:9]=[CH:8][C:7]=2[CH:6]=[C:5](C(=O)C)[CH:4]=1.[N-:15]=[N+:16]=[N-:17].[Na+].Cl.[C:20](#[N:22])[CH3:21]>[Ti](Cl)(Cl)(Cl)Cl>[CH3:21][C:20]1[N:22]([C:5]2[CH:4]=[C:3]([CH2:2][OH:1])[C:11]3[O:10][CH:9]=[CH:8][C:7]=3[CH:6]=2)[N:17]=[N:16][N:15]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 33557Sodium AzideHCID 212208891-(7-Hydroxymethyl-benzofuran-5-yl)-ethanone

生成物 1

HCID 21220940[5-(5-Methyl-tetrazol-1-yl)-benzofuran-7-yl]-methanol

試薬・触媒・溶媒 1

HCID 24193Titanium Tetrachloride触媒

実験手順

A solution of 1-(7-hydroxymethyl-benzofuran-5-yl)-ethanone (250 mg,) and sodium azide (0.68 g) in acetonitrile (40 ml) was treated with titanium tetrachloride (0.29 ml) and heated at reflux for 1.5 h. The reaction mixture was allowed to cool, treated with 2N hydrochloric acid (40 ml) and extracted with ethyl acetate (2×40 ml). The organic phases were dried, combined, filtered and the filtrate evaporated in vacuo to give a yellow oil. Purification by FCC eluted with hexane:ethyl acetate (1:3) gave the title compound as a clear gum (131 mg).

後処理

  1. temperatureheated
  2. temperatureat reflux for 1.5 h
  3. temperatureto cool
  4. extractionextracted with ethyl acetate (2×40 ml)
  5. customThe organic phases were dried
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo
  8. customto give a yellow oil
  9. customPurification by FCC
  10. washeluted with hexane:ethyl acetate (1:3)

出典と根拠

ORDレコード
ord-70632d6ab6754a7c916f98c3a18bc8b4
出典データセット
uspto-grants-1999_08
特許番号
US05935972

反応ノート

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