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

HRID 1584777노트

반응식

HRID 1584777 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 24193Titanium Tetrachloride촉매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-70632d6ab6754a7c916f98c3a18bc8b4
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05935972

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