2-Propyn-1-ol, 3-(trimethylsilyl)- → HCID 66704184, compound

HRID 424778Notes

Reaction equation

HRID 424778 reaction equation
[N:1]([C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:11])=[N+:2]=[N-:3].C[Si](C)(C)[C:14]#[C:15][CH2:16][OH:17]>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:11][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([Cl:10])[C:4]=1[N:1]1[C:15]([CH2:16][OH:17])=[CH:14][N:3]=[N:2]1

Participants

5

Reactant 2

HCID 789302-Propyn-1-ol, 3-(trimethylsilyl)-HCID 116008082-Azido-1,3-dichloro-benzene

Product 1

HCID 66704184HCID 66704184, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-azido-1,3-dichloro-benzene (4.00 g, 1 equiv) and 3-trimethylsilanyl-prop-2-yn-1-ol (6.29 mL, 2 equiv) in toluene (10 mL) is heated to 120° C. for 23 h. The reaction mixture is allowed to cool to room temperature and is diluted with 100 mL methylene chloride. The solution is adsorbed onto diatomaceous earth and is purified via flash chromatography eluting with hexanes/ethyl acetate (85:15 to 20:80) to give [3-(2,6-Dichloro-phenyl)-3H-[1,2,3]triazol-4-yl]-methanol (2.30 g, 44%) as an off-white solid.

Workup

  1. customis purified via flash chromatography
  2. washeluting with hexanes/ethyl acetate (85:15 to 20:80)

Sources & evidence

ORD record
ord-4a1092523785402cb704fdb4ce39eb38
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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