Boron trifluoride etherate → HCID 17932014, compound

HRID 2369220Notes

Reaction equation

HRID 2369220 reaction equation
[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]

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 21197492HCID 21197492, compound2×

Product 1

HCID 17932014HCID 17932014, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8078CyclohexaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f08779cd864644bea82ac0a211c2d606
Source dataset
uspto-grants-2014_04
Patent number
US08703937B2

Reaction notes

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