Boron trifluoride etherate → HCID 9992883, compound

HRID 2287456Notes

Reaction equation

HRID 2287456 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].B(F)(F)F.CCOCC.[CH3:20][C:21]1([CH:27]=[CH2:28])[O:26][C:24](=[O:25])[CH2:23][CH2:22]1>O1CCOCC1.CCOCC>[CH3:20][C:21]1([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH2:27][CH2:28][C:4]2[C:3](=[C:2]([CH3:1])[C:7]([CH3:8])=[CH:6][C:5]=2[CH3:9])[O:10]1

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 127692,3,5-TrimethylphenolHCID 1025504-HYDROXY-4-METHYL-5-HEXENOIC ACID gamma LACTONE

Product 1

HCID 9992883HCID 9992883, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 2,3,5-trimethylphenol (0.01 mol) and boron trifluoride diethyl etherate (0.016 mol) in dioxane (10 mL, dried on sodium) in a flask was added γ-methyl-γ-vinylbutyrolactone (0.016 mol) in dioxane (5.0 mL) via syringe pump over 50 min at 110° C. (oil bath, reflux) under nitrogen. The reaction mixture was cooled to room temperature and diluted with ether (200 mL), then washed with water (100 mL, 2×50 mL) and dried over sodium sulfate. Ether was then removed in vacuum. The residue was dissolved in methanol (30 mL), and solvent was removed in vacuum. The reaction mixture was purified by flash column chromatography on silica gel (eluent ethyl acetate/hexane, 1:1). Fractions containing the desired chroman were pooled, solvent was removed, and the compound was crystallized from ethyl acetate/hexane to afford a white crystalline product in a yield of 40%. M.P.: 148-149° C.

Workup

  1. temperature(oil bath, reflux) under nitrogen
  2. washwashed with water (100 mL, 2×50 mL)
  3. dry with materialdried over sodium sulfate
  4. customEther was then removed in vacuum
  5. dissolutionThe residue was dissolved in methanol (30 mL)
  6. customsolvent was removed in vacuum
  7. customThe reaction mixture was purified by flash column chromatography on silica gel (eluent ethyl acetate/hexane, 1:1)
  8. additionFractions containing the desired chroman
  9. customsolvent was removed
  10. customthe compound was crystallized from ethyl acetate/hexane
  11. customto afford a white crystalline product in a yield of 40%

Sources & evidence

ORD record
ord-df787235a0bc4255883c0008a08491bf
Source dataset
uspto-grants-2000_07
Patent number
US06083982

Reaction notes

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