Imidazole → 2-Phenoxyethyl 3-tert-butyldimethylsiloxybenzoate

HRID 990608Notes

Reaction equation

HRID 990608 reaction equation
CN(C)C=O.[OH:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[C:10]([O:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:11].[C:25]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])([CH3:27])[CH3:26].N1C=CN=C1>O>[O:6]([C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[C:10]([O:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:11])[Si:29]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 135053562-Phenoxyethyl 3-hydroxybenzoate

Product 1

HCID 233915782-Phenoxyethyl 3-tert-butyldimethylsiloxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 250 mL round bottom flask was added 30 mL of dry dimethyl formamide. Five parts of hydroxy ester (53) and 3.5 parts of tert-butyldimethyl silyl chloride were added. to the reaction flask with stirring. Three parts of Imidazole was added in portions and stirring was continued for 10 hours. The reaction mixture was diluted with 80 mL of water and the product was extracted with ethyl acetate. The organic layer was washed with water and dried on anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an oil, yield 6.80 parts. This material was pure enough for next step of the reaction. The reaction proceeded as follows:

Workup

  1. stirringstirring
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customto give an oil
  7. customyield 6.80 parts
  8. customThis material was pure enough for next step of the reaction

Sources & evidence

ORD record
ord-b7683dff1673461b8faa54f02a6411a3
Source dataset
uspto-grants-2002_10
Patent number
US06461876B1

Reaction notes

Loading…