Imidazole → 5-Benzyloxy-2-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-benzoic acid methyl ester

HRID 572488Notes

Reaction equation

HRID 572488 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[C:18]#[C:19][CH2:20][OH:21].N1C=CN=C1.[CH3:28][C:29]([Si:32](Cl)([CH3:34])[CH3:33])([CH3:31])[CH3:30]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=[CH:6][C:5]=1[C:18]#[C:19][CH2:20][O:21][Si:32]([C:29]([CH3:31])([CH3:30])[CH3:28])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 682958095-Benzyloxy-2-(3-hydroxy-prop-1-ynyl)-benzoic acid methyl ester

Product 1

HCID 682952775-Benzyloxy-2-[3-(tert-butyl-dimethyl-silanyloxy)-prop-1-ynyl]-benzoic acid methyl esterYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-Benzyloxy-2-(3-hydroxy-prop-1-ynyl)-benzoic acid methyl ester (80 g, 270 mmol) in DCM (1.5 L) was added imidazole (36.8 g, 540 mmol) and TBSCl (61 g, 405 mmol). The mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with water, brine, dried over Na2SO4 and concentrated to dryness. The residue was purified by chromatography column on silica gel to afford title product (90 g, 81%).

Workup

  1. washThe reaction mixture was washed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by chromatography column on silica gel

Sources & evidence

ORD record
ord-21b5e9983fc94372a7b26ce7162b9054
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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