Boron trifluoride etherate → HCID 23442880, compound

HRID 2119729Notes

Reaction equation

HRID 2119729 reaction equation
[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([OH:15])=[C:7]([CH:16](O)[CH:17]([CH3:19])[CH3:18])[C:6]=1[CH3:21])(=[O:3])[CH3:2].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]2[O:15][C:17]([CH3:19])([CH3:18])[CH2:16][C:7]=2[C:6]=1[CH3:21])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 23442862HCID 23442862, compound

Product 1

HCID 23442880HCID 23442880, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.40 g of 4-acetoxy-5-t-butyl-2-(1-hydroxy-2-methylpropyl)-3-methylphenol was dissolved in 10 ml of anhydrous toluene, 0.35 ml of boron trifluoride ethyl ether was added dropwise, and the mixture was stirred at room temperature for a whole day and night. After the reaction was quenched with water, the mixture was extracted with ethyl acetate. The organic layers were washed with a saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 1%-2% ethyl acetate) to give 70 mg of 5-acetoxy-6-t-butyl-2,2,4-trimethyl-2,3-dihydrobenzofuran as a pale yellow oil (yield 19%).

Workup

  1. customAfter the reaction was quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layers were washed with a saturated aqueous sodium bicarbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 1%-2% ethyl acetate)

Sources & evidence

ORD record
ord-4ca9b55d7b494be68180f4ed1b7d0a08
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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