Boron trifluoride etherate → HCID 17932014, 화합물

HRID 2369220노트

반응식

HRID 2369220 반응식
[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]

참가 물질

7

반응물 4

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 21197492HCID 21197492, 화합물2회

생성물 1

HCID 17932014HCID 17932014, 화합물

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8078Cyclohexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f08779cd864644bea82ac0a211c2d606
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703937B2

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