Butyryl chloride → (4S)-3-Butanoyl-4-(propan-2-yl)-1,3-oxazolidin-2-one

HRID 326915ノート

反応式

HRID 326915 の反応式
[CH3:1][CH:2]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)[CH3:3].[Li]CCCC.[C:15](Cl)(=[O:19])[CH2:16][CH2:17][CH3:18].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[O:19]=[C:15]([N:5]1[C@@H:4]([CH:2]([CH3:3])[CH3:1])[CH2:8][O:7][C:6]1=[O:9])[CH2:16][CH2:17][CH3:18]

参加物

6

反応物 4

HCID 8855Butyryl chlorideHCID 11430Potassium CarbonateHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-oneHCID 178418339Butyllithium

生成物 1

HCID 10330387(4S)-3-Butanoyl-4-(propan-2-yl)-1,3-oxazolidin-2-one収率 104.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A mechanically stirred, cooled (-78° C.) solution of the oxazolidinone of Step 5 (32.3 g, 250 mmol) in anhydrous THF (830 mL) was metalated with 163 mL (1.6M in hexane, 261 mmol) of n-BuLi and treated with freshly distilled butanoyl chloride (28.1 mL, 271 mmol). The reaction mixture was warmed to 0° C. and stirred for 0.5 h. Excess acid chloride was hydrolyzed by the addition of 1M aqueous K2CO3 (165 mL) followed by stirring the resultant two-phase mixture for 1 h at r.t. Volatiles were removed in vacuo and the product was extracted into CH2Cl2 (3x). The combined organic extracts were successively washed with H2O and brine, dried over MgSO4 and concentrated to give the title compound as a pale yellow oil (52.1 g, quantative). A portion of this crude product was purified by flash chromatography on silica with EtOAc:hexane 1:4 to give a colorless liquid.

後処理

  1. stirringstirred for 0.5 h
  2. customVolatiles were removed in vacuo
  3. extractionthe product was extracted into CH2Cl2 (3x)
  4. washThe combined organic extracts were successively washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-3442133adfa947e99a2c199eb5225e8c
出典データセット
uspto-grants-1993_12
特許番号
US05270324

反応ノート

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