Hydrochloric Acid → [1-(Triphenylmethyl)-1H-1,2,3-triazol-4-yl]methanol

HRID 249613Notes

Reaction equation

HRID 249613 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[N:12]=[N:13][N:14]([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=1)=O.Cl>O1CCCC1>[C:16]([N:14]1[CH:15]=[C:11]([CH2:9][OH:8])[N:12]=[N:13]1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 17878067HCID 17878067, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13471695[1-(Triphenylmethyl)-1H-1,2,3-triazol-4-yl]methanolYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (6.17 g : 0.163 Mol.) in tetrahydrofuran ( 600 ml) under ice cooling is added 1-trityl-1,2,3- triazol-4-ylcarboxylic acid methyl ester (40.0 g : 0.108 Mol.), and the mixture is stirred at room temperature for 1 hour. To the reaction mixture is added dropwise aqueous tetrahydrofuran under ice cooling. The mixture is neutralized with 10% hydrochloric acid, filtered to remove insoluble material, diluted with ethyl acetate, washed with brine, dried over sodium sulfate, and concentrated. The resulting crystals are washed with ether to give 1-trityl-1,2,3-triazol-4-yl- methanol (33.4 g) as white crystals. Yield: 91%. mp. 200° to 201° C. NMR δ (CDCl3) ppm: 2.4-2.9(brs, 1H), 4.76(s, 2H), 7.05-7.15(m, 6H), 7.3-7.4(m, 9H), 7.43(s, 1H).

Workup

  1. filtrationfiltered
  2. customto remove insoluble material
  3. additiondiluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. washThe resulting crystals are washed with ether

Sources & evidence

ORD record
ord-9b4931793c7c46989473ad674cab93ef
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Reaction notes

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