Boron trifluoride etherate → HCID 19737804, compound

HRID 258409Notes

Reaction equation

HRID 258409 reaction equation
[CH3:1][C:2]1[C:3]([CH2:13][C:14]([CH3:16])=[CH2:15])=[C:4]([OH:12])[C:5]([CH2:9][CH:10]=[CH2:11])=[C:6]([CH3:8])[CH:7]=1.B(F)(F)F.CCOCC.C(=O)([O-])O.[Na+]>ClCCCl>[CH3:15][C:14]1([CH3:16])[O:12][C:4]2[C:5]([CH2:9][CH:10]=[CH2:11])=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]=2[CH2:13]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 19781063HCID 19781063, compound

Product 1

HCID 19737804HCID 19737804, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2.44 g (11.3 mmol) of 3,5-dimethyl-2-(2-methyl-2-propen-1-yl)-6-(2-propen-1-yl)phenol (Compound No. 1) was dissolved in 20 ml of 1,2-dichloroethane, and 0.42 ml (3.39 mmol) of boron trifluoride etherate was added thereto at 0° C. The above mixture was then stirred in an atmosphere of argon gas for 4 hours, poured into an aqueous solution of sodium hydrogencarbonate, and extracted with ethyl acetate. The thus obtained extract layer was washed successively with water and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and then concentrated, whereby 2.37 g of a crude 2,3-dihydro-2,2,4,6-tetramethyl-7-(2-propen-1-yl)benzo[b]furan (Compound No. 2) was obtained as a yellow oily material.

Workup

  1. customat 0° C
  2. extractionextracted with ethyl acetate
  3. customThe thus obtained
  4. extractionextract layer
  5. washwas washed successively with water
  6. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-385c321d986e4db68dd1c868748888aa
Source dataset
uspto-grants-1993_11
Patent number
US05266707

Reaction notes

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