Tetrahydrofuran → 1-butyl-1H-benzotriazole-5-methanol

HRID 2166036Notes

Reaction equation

HRID 2166036 reaction equation
[AlH4-].[Li+].O1CCCC1.[CH2:8]([N:12]1[C:16]2[CH:17]=[CH:18][C:19]([C:21](O)=[O:22])=[CH:20][C:15]=2[N:14]=[N:13]1)[CH2:9][CH2:10][CH3:11]>O>[CH2:8]([N:12]1[C:16]2[CH:17]=[CH:18][C:19]([CH2:21][OH:22])=[CH:20][C:15]=2[N:14]=[N:13]1)[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 28112Lithium aluminum hydrideHCID 103310191-Butyl-1,2,3-benzotriazole-5-carboxylic acid

Product 1

HCID 149905701-butyl-1H-benzotriazole-5-methanolYield 42.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and cooled (0° C.) suspension of 23.4 parts of lithium tetrahydroaluminate in 270 parts of dry tetrahydrofuran were added portionwise 45 parts of 1-butyl-1H-benzotriazole-5-carboxylic acid. Upon complete addition, stirring was continued for 1 hour at 0° C. The reaction mixture was hydrolysed with 50 parts of water. The whole was filtered and washed with a mixture of dichloromethane and methanol (90:10 by volume). The filtrate was evaporated to dry and the residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 18 parts (42.7%) of 1-butyl-1H-benzotriazole-5-methanol as an oily residue (int. 10).

Workup

  1. temperaturecooled
  2. additionUpon complete addition
  3. stirringstirring
  4. filtrationThe whole was filtered
  5. washwashed with a mixture of dichloromethane and methanol (90:10 by volume)
  6. customThe filtrate was evaporated
  7. customto dry
  8. customthe residue was purified by column chromatography over silica gel using
  9. additiona mixture of dichloromethane and methanol (98:2 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated

Sources & evidence

ORD record
ord-4f5f8180b03841989e8efd4abb7f354b
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

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