Sodium hydride → HCID 76739653、化合物

HRID 2189061ノート

反応式

HRID 2189061 の反応式
[C@H:1]1([OH:7])[CH:5]=[CH:4][C@@H:3]([OH:6])[CH2:2]1.[H-].[Na+].[C:10]([O:14][C:15](=[O:18])[CH2:16]Br)([CH3:13])([CH3:12])[CH3:11]>CN(C=O)C.C1COCC1>[C:10]([O:14][C:15](=[O:18])[CH2:16][O:6][CH:3]1[CH2:2][CH:1]([OH:7])[CH:5]=[CH:4]1)([CH3:13])([CH3:12])[CH3:11]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 10148988cis-4-Cyclopentene-1,3-Diol

生成物 1

HCID 76739653HCID 76739653、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Dissolve 2.0 g (20 mmol) of cis-4-cyclopentene-1,3-diol in 1.5 ml of DMF and 15 ml of THF and, at 0° C., add 799 mg (60% strength, approx. 20 mmol) of sodium hydride in portions. After the end of the addition, warm the mixture to RT and stir at RT for a further 1 h, before adding 2.7 ml (18.2 mmol) of bromoacetic acid tert-butyl ester. Then stir the mixture at RT overnight. Then add water, extract with dichloromethane, wash the organic phase with satd. sodium chloride solution, concentrate under reduced pressure and dry the residue under high vacuum. Isolate the product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1→2:1). 1.10 g (25.6% of theory) of the target compound are obtained.

後処理

  1. additionAfter the end of the addition
  2. stirringThen stir the mixture at RT overnight
  3. extractionThen add water, extract with dichloromethane
  4. washwash the organic phase with satd
  5. concentrationsodium chloride solution, concentrate under reduced pressure
  6. customdry the residue under high vacuum
  7. customIsolate the product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1→2:1)
  8. custom1.10 g (25.6% of theory) of the target compound are obtained

出典と根拠

ORDレコード
ord-e53ea661c1784d0d83c7b2e62c186668
出典データセット
uspto-grants-2012_12
特許番号
US08324222B2

反応ノート

読み込み中…