Water → 3-(2-Fluoro-4-nitrobenzyl)-1,3-oxazolidin-2-one

HRID 241755ノート

反応式

HRID 241755 の反応式
[H-].[Na+].[O:3]1[CH2:7][CH2:6][NH:5][C:4]1=[O:8].Br[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[F:20].O>C1COCC1.CN(C=O)C>[F:20][C:12]1[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:11]=1[CH2:10][N:5]1[CH2:6][CH2:7][O:3][C:4]1=[O:8]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 739492-OxazolidinoneHCID 218861321-(Bromomethyl)-2-fluoro-4-nitrobenzene

生成物 1

HCID 666368043-(2-Fluoro-4-nitrobenzyl)-1,3-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 21974620tetrahydrofuran N,N-dimethylformamide溶媒3 回

実験手順

To a suspension of sodium hydride 60% in oil (4.48 mmoles) in a mixture of THF/DMF (2.7 ml/0.45 ml) at 0° C. under an inert atmosphere there is added, dropwise, a solution of 1,3-oxazolidin-2-one (24.1 mmoles) in a mixture of THF/DMF (71 ml/5.6 ml) over 30 minutes. After stiffing for 1 hour, a solution of the compound obtained in Step A (26.5 mmoles) in a mixture of THF/DMF (56 ml/11.2 ml) is added over 1.5 hours, maintaining the temperature below 10° C. Stirring is maintained for 1.5 hours. Water (12 ml) is slowly added to the reaction mixture and then the THF is removed under reduced pressure. The reaction mixture is diluted with saturated aqueous NaCl solution and then extracted 3 times with 100 ml of AcOEt. The organic phases are combined, washed with saturated aqueous NaCl solution and then dried with MgSO4. After filtration, the organic phase is evaporated to dryness. The residue is purified on silica gel (SiO2, eluant CH2Cl2) to yield the title product which is used directly in the next Step.

後処理

  1. additionis added
  2. additionis added over 1.5 hours
  3. temperaturemaintaining the temperature below 10° C
  4. temperatureis maintained for 1.5 hours
  5. customthe THF is removed under reduced pressure
  6. additionThe reaction mixture is diluted with saturated aqueous NaCl solution
  7. extractionextracted 3 times with 100 ml of AcOEt
  8. washwashed with saturated aqueous NaCl solution
  9. dry with materialdried with MgSO4
  10. filtrationAfter filtration
  11. customthe organic phase is evaporated to dryness
  12. customThe residue is purified on silica gel (SiO2, eluant CH2Cl2)

出典と根拠

ORDレコード
ord-f8117776bce54a23aa27db982d49a473
出典データセット
uspto-grants-2014_02
特許番号
US08653073B2

反応ノート

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