Imidazole → Ethyl 4-{[tris(1-methylethyl)silyl]oxy}benzoate

HRID 2400543Notes

Reaction equation

HRID 2400543 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.N1C=CN=C1.Cl[Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21].O>CN(C=O)C>[CH3:21][CH:20]([Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1)[CH3:22]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 8434EthylparabenHCID 139400Triisopropylsilyl chloride

Product 1

HCID 59504619Ethyl 4-{[tris(1-methylethyl)silyl]oxy}benzoateYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4-hydroxybenzoate (5.0 g, 30.1 mmol) and imidazole (2.4 g, 35.4 mmol) in dry DMF (20 mL) was added chlorotriisopropylsilane (6.8 mL, 31 mmol) dropwise at 0° C. The mixture was stirred at rt for 16 h. Then water was added (100 mL), and the product was extracted with diethyl ether (3×100 mL). The combined organic extracts were washed with brine and dried over anhydrous magnesium sulfate. After filtration and evaporation of the solvent, the remaining crude product was purified by MPLC (silica, cyclohexane/ethyl acetate 10:1→1:1) to afford the title compound (9.66 g, 99%): 1H NMR (400 MHz, CDCl3) δ 7.93 (d, 2H), 6.89 (d, 2H), 4.33 (quart, 2H), 1.38 (t, 3H), 1.27 (m, 1H), 1.10 (d, 18H); DCI(NH3)-MS m/z 323 (MH)+; HPLC RT (Method G) 6.19 min.

Workup

  1. extractionthe product was extracted with diethyl ether (3×100 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration and evaporation of the solvent
  5. customthe remaining crude product was purified by MPLC (silica, cyclohexane/ethyl acetate 10:1→1:1)

Sources & evidence

ORD record
ord-d9838f8a22d9441087e8f189234d662d
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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