Benzyl chloroformate → HCID 23497522、化合物

HRID 1837081ノート

反応式

HRID 1837081 の反応式
[CH2:1]([O:3][CH:4]([O:6][CH2:7][CH2:8][C:9]#[CH:10])[CH3:5])[CH3:2].C([Li])CCC.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>O1CCCC1>[CH2:1]([O:3][CH:4]([O:6][CH2:7][CH2:8][C:9]#[C:10][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH3:5])[CH3:2]

参加物

5

反応物 3

HCID 10387Benzyl chloroformateHCID 131717324-(1-Ethoxyethoxy)-1-butyneHCID 178418339Butyllithium

生成物 1

HCID 23497522HCID 23497522、化合物収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

The product from Example 31A (79.99 g, 0.563 mole) in tetrahydrofuran (1 L) was treated dropwise at −78° C. with n-butyllithium (2.5 M in hexane, 0.563 mole, 225 mL). The reaction mixture was stirred at −78° C. for 30 minutes and then benzyl chloroformate (0.563 mole, 80.4 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 2 hours, allowed to warm to ambient temperature and stirred overnight. After quenching with water, ethyl acetate was added and the layers were separated. The organic layer was dried over magnesium sulfate, filtered and concentrated. Flash chromatography of the residue (silica, hexane to hexane:ethyl acetate, 30:1 to 4:1) provided the title compound as a colorless oil (155.5 g, 78%).

後処理

  1. stirringThe reaction mixture was stirred at −78° C. for 2 hours
  2. temperatureto warm to ambient temperature
  3. stirringstirred overnight
  4. customAfter quenching with water, ethyl acetate
  5. additionwas added
  6. customthe layers were separated
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-bca14c13d81145fbbc3a7ea5099a2f79
出典データセット
uspto-grants-2004_08
特許番号
US06780872B2

反応ノート

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