Aluminium lithium hydride → HCID 18438076, compound

HRID 457356Notes

Reaction equation

HRID 457356 reaction equation
C([O:5][C:6]([C:8]1[N:12]([CH2:13][CH2:14][CH2:15][CH3:16])[C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:10][N:9]=1)=O)CCC.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:13]([N:12]1[C:11]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:10][N:9]=[C:8]1[CH2:6][OH:5])[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66757257HCID 66757257, compound

Product 1

HCID 18438076HCID 18438076, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Butyl-5-phenyl-4H-[1,2,4]triazole-3-carboxylic acid butyl ester (169) (1.38 g, 5 mmol) is taken up in 50 ml anhydrous THF. LAH is added (3 eq.). The reaction is refluxed for 12 hours and then quenched carefully with water. Purification by column with 2.5% MeOH/DCM gives the desired product (170). 1HNMR(CDCl3): δ=7.40–7.60(5H, m, phenyl-H), 4.88(2H, s, —CH2OH), 4.26(1H, br, —OH), 4.10(2H, t, J=7.8 Hz, —CH2—), 1.58–1.70(2H, m, —CH2—), 1.08–1.30(2H, m, —CH2—), 0.82(3H, t, J=7.5 Hz, —CH3)

Workup

  1. temperatureThe reaction is refluxed for 12 hours
  2. customquenched carefully with water
  3. customPurification by column with 2.5% MeOH/DCM

Sources & evidence

ORD record
ord-09ef39be91fb4e83a958b367912376bf
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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