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

HRID 1768053Notes

Reaction equation

HRID 1768053 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-e62b3c0882c34dee962c3f73ce3e85f4
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

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