Ethylene Glycol → HCID 68160183, compound

HRID 1468755Notes

Reaction equation

HRID 1468755 reaction equation
[Si:1]([O:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:18](O)[CH2:19][OH:20]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:4]([Si:1]([CH3:3])([CH3:2])[O:8][CH2:9][C:10]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:20][CH2:19][CH2:18][O:11]1)([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 135233382-(Tert-butyldimethylsilanyloxy)-1-phenylethanone

Product 1

HCID 68160183HCID 68160183, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

2-(tert-Butyldimethylsilanyloxy)-1-phenylethanone (8.0 g, 32 mmol), ethylene glycol (1.99 g, 32 mmol), and p-toluenesulfonic acid (50 mg) was suspended in benzene (50 ml). The mixture was stirred under reflux for 5 hours. The solvent was evaporated under reduced pressure. The residue was treated with water and ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The crude was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=1/1) to give tert-butyldimethyl-(2-phenyl-[1,3]dioxolan-2-yl-methoxy)silane (5.5 g, 18.7 mmol, 58%) as a yellow oil.

Workup

  1. temperatureunder reflux for 5 hours
  2. customThe solvent was evaporated under reduced pressure
  3. additionThe residue was treated with water and ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe crude was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-93f3c35c28b84cc497ed2dee194b995a
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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