Trityl chloride → 4-{4-[1-(Triphenylmethyl)-1H-1,2,3-triazol-4-yl]butyl}phenol

HRID 750955Notes

Reaction equation

HRID 750955 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:21]1[CH:25]=[C:24]([CH2:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)[N:23]=[N:22]1.C(N(CC)CC)C>CN(C=O)C>[C:7]([N:21]1[CH:25]=[C:24]([CH2:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]([OH:36])=[CH:34][CH:35]=2)[N:23]=[N:22]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178516003HCID 178516003, compound

Product 1

HCID 236145474-{4-[1-(Triphenylmethyl)-1H-1,2,3-triazol-4-yl]butyl}phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 706 mg (5.06 mmol) triphenylchloromethane in 5.0 ml DMF was added at 0° C. to a solution of 500 mg (2.30 mmol) 4-(4-1H-[1,2,3]triazol-4-yl-butyl)-phenol and 512 mg (5.06 mmol) triethylamine in 5.0 ml DMF. The mixture was allowed to reach r.t. overnight and solvents were removed in vacuo. After distribution of the residue between water and ethyl acetate, the organic phase was dried (sodium sulphate), solvents distilled off and the residue purified by column chromatography on silica gel (heptane/ethyl acetate 2:1).

Workup

  1. customsolvents were removed in vacuo
  2. dry with materialAfter distribution of the residue between water and ethyl acetate, the organic phase was dried (sodium sulphate), solvents
  3. distillationdistilled off
  4. customthe residue purified by column chromatography on silica gel (heptane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-8b23e7364f8d43e8acdc9f62518985b1
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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