Hexane → HCID 21187685、化合物

HRID 1383775ノート

反応式

HRID 1383775 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([CH:14]3[CH2:16][CH2:15]3)[O:12][C:11](=[O:17])[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].C([Li])CCC.CCCCCC.[CH:29]1[C:34]([N+:35]([O-:37])=[O:36])=[CH:33][CH:32]=[C:31]([Cl-]C([O-])=O)[CH:30]=1.[C:42](=O)([OH:44])[O-:43].[Na+]>C1COCC1>[N+:35]([C:34]1[CH:29]=[CH:30][C:31]([O:44][C:42]([N:10]2[CH:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=3)[CH:13]([CH:14]3[CH2:15][CH2:16]3)[O:12][C:11]2=[O:17])=[O:43])=[CH:32][CH:33]=1)([O-:37])=[O:36]

参加物

6

反応物 4

HCID 8058HexaneHCID 516892Sodium BicarbonateHCID 22993473HCID 22993473、化合物HCID 178418339Butyllithium

生成物 1

HCID 21187685HCID 21187685、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of 4-(3,4-difluorophenyl)-5-cyclopropyl-oxazolidin-2-one (2 g, 8.3 mmol) in 100 mL THF was added a solution of n-butyllithium in hexane (9.1 mmol) dropwise via a syringe under an argon atmosphere at −78° C. The resulting yellow solution was stirred at −78° C. for 10 min. To this solution was then added dropwise via syringe 4-nitrophenylchloroformate (1.03 g, 5.1 mmol) in 20 mL of THF. The reaction was stirred at −78° for 10 min. The reaction mixture was poured into saturated sodium bicarbonate and extracted with ethyl acetate (2×200 mL). The organic extracts were washed with brine, and the organic layer was dried over Na2SO4. The solvent was removed after filtration, and the residue was purified by column chromatography on silica gel 30% ethyl acetate hexane. The material was rechromatographed on silica gel eluting with 2% acetone/methylene chloride ti) give 1.2 g the product as a thick syrup which solidified upon standing.

後処理

  1. stirringThe reaction was stirred at −78° for 10 min
  2. extractionextracted with ethyl acetate (2×200 mL)
  3. washThe organic extracts were washed with brine
  4. dry with materialthe organic layer was dried over Na2SO4
  5. customThe solvent was removed
  6. filtrationafter filtration
  7. customthe residue was purified by column chromatography on silica gel 30% ethyl acetate hexane
  8. customThe material was rechromatographed on silica gel eluting with 2% acetone/methylene chloride ti)

出典と根拠

ORDレコード
ord-6f9e6bb1a63f43e0846c9ccd65a85520
出典データセット
uspto-grants-2001_07
特許番号
US06255315B1

反応ノート

読み込み中…