Chlorotrimethylsilane → 2-[2-(2-Bromo-5-methoxy-phenyl)-ethyl]-2-phenyl-[1,3]dioxolane

HRID 430851Notes

Reaction equation

HRID 430851 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].Cl[Si](C)(C)[CH3:22].[C:25]([O-:28])(O)=O.[Na+]>C(O)CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:28][CH2:25][CH2:22][O:13]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 113929923-(2-Bromo-5-methoxy-phenyl)-1-phenyl-propan-1-one

Product 1

HCID 98638172-[2-(2-Bromo-5-methoxy-phenyl)-ethyl]-2-phenyl-[1,3]dioxolaneYield 97%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a solution of crude 3-(2-Bromo-5-methoxy-phenyl)-1-phenyl-propan-1-one (19.43 g, 61 mmol) in dry ethylene glycol (300 ml) under a N2 atmosphere was added chlorotrimethylsilane (31 ml, 0.25 mol). The reaction was stirred at room temperature for 1 h. A 5% aqueous NaHCO3 (300 ml) was added. The mixture was extracted with diisopropyl ether, and the extracts were washed with brine. The combined ether extracts were dried with Na2SO4 and the solvent was removed under reduced pressure to produce a weight of 21.52 g crude 2-[2-(2-Bromo-5-methoxy-phenyl)-ethyl]-2-phenyl-[1,3]dioxolane (yield: 97%).

Workup

  1. extractionThe mixture was extracted with diisopropyl ether
  2. washthe extracts were washed with brine
  3. dry with materialThe combined ether extracts were dried with Na2SO4
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4827b171ff054d59ac18543ce3851fc6
Source dataset
uspto-grants-2001_11
Patent number
US06323345B1

Reaction notes

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