Tetrahydrofuran → 4-(2-Hydroxytetrazol-1-yl)-1-benzyloxybenzene

HRID 1809166Notes

Reaction equation

HRID 1809166 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=O)=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C[O:29]CC1>>[OH:29][N:7]1[NH:6][N:5]=[CH:24][N:23]1[C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 33557Sodium AzideHCID 2562684-(Benzyloxy)phenyl isocyanateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 691018424-(2-Hydroxytetrazol-1-yl)-1-benzyloxybenzene

Procedure

To a 100 mL recovery flask was added THF (20 mL) and a stirbar. The flask was cooled to 0° C. whereupon AlCl3 (751 mg, 5.63 mmol, 1.1 eq.) was added. The solution was stirred for 15 min whereupon NaN3 (1.00 g, 15.4 mmol, 3.0 eq.) and 4-benzyloxy-phenylisocyanate 51 (1.15 g, 5.12 mmol, 1.0 eq.) was added. The reaction mixture was refluxed overnight. The reaction mixture was quenched with 1N HCl (50 mL) and diluted with EtOAc (100 mL). The organic phases were washed with brine and the combined aqueous phases were extracted with EtOAc (3×50 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated to give an off-white solid that was used in subsequent reactions without further purification. (515 mg, 37%)

Workup

  1. additionwas added
  2. additionwas added
  3. temperatureThe reaction mixture was refluxed overnight
  4. customThe reaction mixture was quenched with 1N HCl (50 mL)
  5. additiondiluted with EtOAc (100 mL)
  6. washThe organic phases were washed with brine
  7. extractionthe combined aqueous phases were extracted with EtOAc (3×50 mL)
  8. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give an off-white solid that
  12. customwas used in subsequent reactions without further purification

Sources & evidence

ORD record
ord-d0d98ee287c54c0a8131e1f12c365708
Source dataset
uspto-grants-2013_01
Patent number
US08362017B2

Reaction notes

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