Boron trifluoride etherate → HCID 17932014、化合物

HRID 2369220ノート

反応式

HRID 2369220 の反応式
[CH2:1]([O:8][C:9](=[O:17])[CH2:10][CH2:11][CH:12]([Br:16])[C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C(=N)O[C:22]([CH3:25])([CH3:24])[CH3:23].B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C1CCCCC1>[Br:16][CH:12]([CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:17])[C:13]([O:15][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:14]

参加物

7

反応物 4

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 21197492HCID 21197492、化合物2 回

生成物 1

HCID 17932014HCID 17932014、化合物

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8078Cyclohexane溶媒

実験手順

5-(Benzyloxy)-2-bromo-5-oxopentanoic acid, 10.0 g (0.033 mole), was dissolved in chloroform, 20 mL. To this was added a solution of t-butyl trichloroacetimidate, 15.9 g (0.073 mole), dissolved in cyclohexane, 50 mL, drop-wise over 30 minutes. The mixture was allowed to stir an additional 5 minutes and boron trifluoride etherate, 100 μL, was added. The reaction mixture was allowed to stir overnight. Sodium bicarbonate, 5 g, was added. After stirring 10 minutes, hexanes, 50 mL, was added and the mixture filtered to remove the solids present. The filtrate was evaporated and the residue purified by flash chromatography, ethyl acetate-hexanes, to give a clear-colorless oil. The yield was 8.2 g, 69% based on starting 5-(Benzyloxy)-2-bromo-5-oxopentanoic acid. NMR is consistent with structure.

後処理

  1. stirringto stir overnight
  2. stirringAfter stirring 10 minutes
  3. filtrationthe mixture filtered
  4. customto remove the solids present
  5. customThe filtrate was evaporated
  6. customthe residue purified by flash chromatography, ethyl acetate-hexanes
  7. customto give a clear-colorless oil

出典と根拠

ORDレコード
ord-f08779cd864644bea82ac0a211c2d606
出典データセット
uspto-grants-2014_04
特許番号
US08703937B2

反応ノート

読み込み中…