Sodium hydride → 4-((3-(Triethoxysilyl)propoxy)methyl)phenyl benzoate

HRID 1841844Notes

Reaction equation

HRID 1841844 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:21][CH2:22][CH2:23][Si:24]([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27]>O1CCCC1>[C:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][O:17][CH2:21][CH2:22][CH2:23][Si:24]([O:25][CH2:26][CH3:27])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11782516(3-Iodopropyl)triethoxysilaneHCID 131816394-(Hydroxymethyl)phenyl benzoate

Product 1

HCID 529114704-((3-(Triethoxysilyl)propoxy)methyl)phenyl benzoateYield 30.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-(Hydroxymethyl)phenyl benzoate (1 g, 4.39 mmol) was dissolved in 20 mL of anhydrous tetrahydrofuran and cooled in an ice bath. A suspension of sodium hydride (60% suspension, 175 mg, 4.39 mmol) in 5 mL of anhydrous tetrahydrofuran was added dropwise under stirring. The resultant mixture was stirred at 0° C. for 1 hour. (3-Iodopropyl)triethoxysilane (1.46 g, 4.39 mmol) was added and the mixture was refluxed for 36 hours. The reaction crude was filtered, the solvent was removed under reduced pressure, and the resultant oil was chromatographed (hexane/ethyl acetate 8:2) thus affording 570 mg (1.32 mmol, yield=30%) of the title compound (HPLC purity=99.2%).

Workup

  1. temperaturecooled in an ice bath
  2. additionwas added dropwise
  3. temperaturethe mixture was refluxed for 36 hours
  4. customThe reaction crude
  5. filtrationwas filtered
  6. customthe solvent was removed under reduced pressure
  7. customthe resultant oil was chromatographed (hexane/ethyl acetate 8:2)

Sources & evidence

ORD record
ord-3f3be5e5e1ea47d6a2fc0f5d02a3e860
Source dataset
uspto-grants-2015_02
Patent number
US08945522B2

Reaction notes

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