Tetrahydrofuran → (S)-4-isopropyl-3-(4-pentenoyl)-oxazolidin-2-one

HRID 1079024

反応式

HRID 1079024 の反応式
[CH3:1][CH:2]([CH:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)[CH3:3].C([Li])CCC.[CH2:15](Cl)[CH2:16][CH2:17][CH:18]=[CH2:19].[O:21]1CCCC1>CCCCCC.[Cl-].[NH4+].C(OCC)C>[CH3:1][CH:2]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:15](=[O:21])[CH2:16][CH2:17][CH:18]=[CH2:19])[CH3:3]

参加物

8

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 5193532-Oxazolidinone, 4-(1-methylethyl)-HCID 5230425-Chloro-1-penteneHCID 178418339Butyllithium

生成物 1

HCID 11820460(S)-4-isopropyl-3-(4-pentenoyl)-oxazolidin-2-one

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒HCID 25517Ammonium Chloride溶媒

実験手順

To a -78° C. solution of 5.0 g of 4-(1-methylethyl)-2-oxazolidinone in 80 ml of tetrahydrofuran is added, dropwise, 15.5 ml of 2.5M n-butyl lithium in hexane. After stirring for 30 minutes, a solution of 4.8 g of 4-pentenyl chloride in 30 ml of tetrahydrofuran is added, dropwise, and the resulting solution is stirred at -78° C. for 3.5 hours. The reaction is diluted with aqueous ammonium chloride and diethyl ether. The organic layer is washed with water, dried and concentrated in vacuo. The residue is purified by chromatography (silica gel, 25% ethyl acetate/petroleum ether) to give 5.8 g of the desired product as a pale yellow oil. [α]D26 =+79° (methylene chloride).

後処理

  1. stirringdropwise, and the resulting solution is stirred at -78° C. for 3.5 hours
  2. washThe organic layer is washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography (silica gel, 25% ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-883850b5833e4156a9217c614cda6f9f
出典データセット
uspto-grants-1996_08
特許番号
US05550257

関連ノート

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