Ethylene Oxide → 3-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]oxazolidin-2-one

HRID 626074Notes

Reaction equation

HRID 626074 reaction equation
[CH2:1]([O:8][C:9](=[O:35])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][C:19]=2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:13]([F:34])[CH:12]=1)[C:2]1C=CC=CC=1.C([Li])CCC.C1OC1>O1CCCC1>[CH2:27]([O:26][C:19]1[CH:20]=[C:21]([CH2:24][CH3:25])[CH:22]=[CH:23][C:18]=1[O:17][C:14]1[CH:15]=[CH:16][C:11]([N:10]2[CH2:2][CH2:1][O:8][C:9]2=[O:35])=[CH:12][C:13]=1[F:34])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 59191307[4-(2-Benzyloxy-4-ethyl-phenoxy)-3-fluoro-phenyl]-carbamic acid benzyl esterHCID 178418339Butyllithium

Product 1

HCID 591913503-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]oxazolidin-2-oneYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]-carbamic acid-benzyl ester (500 mg, 1.06 mmol) in 5 ml tetrahydrofuran under nitrogen atmosphere was cooled to −78° C. To this added 2.8M n-butyl lithium (0.075 g, 1.16 mmol) dropwise and the stirring at −78° C. for 1 h. Condensed ethylene oxide (0.5 ml, 9.9 mmol) was then added dropwise to the reaction mixture and warmed slowly to rt. The reaction was stirred at rt overnight and then quenched with saturated ammonium chloride solution. The aqueous phase was extracted with dichloromethane and the combined organic phase was dried over anhydrous Na2SO4 and concentrated. The crude obtained was purified by column chromatography on silica gel using 25% ethyl acetate in petroleum ether as eluant to obtain 350 mg, 81% of the title compound as a brown oil.

Workup

  1. additionwas then added dropwise to the reaction mixture
  2. customquenched with saturated ammonium chloride solution
  3. extractionThe aqueous phase was extracted with dichloromethane
  4. dry with materialthe combined organic phase was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe crude obtained
  7. customwas purified by column chromatography on silica gel using 25% ethyl acetate in petroleum ether as eluant

Sources & evidence

ORD record
ord-63047eb77570487d9b20c741405a97c5
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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