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

HRID 1584777Notes

Reaction equation

HRID 1584777 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-70632d6ab6754a7c916f98c3a18bc8b4
Source dataset
uspto-grants-1999_08
Patent number
US05935972

Reaction notes

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