Boron trifluoride → 5-Acetoxy-2,2-diisoamyl-4,6-di-tert-butyl-2,3-dihydrobenzofuran

HRID 1452373Notes

Reaction equation

HRID 1452373 reaction equation
B(F)(F)F.[C:5]([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][C:12]([OH:19])=[C:11]([CH:20](O)[CH:21]([CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[C:10]=1[C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:7])[CH3:6].C(=O)([O-])O.[Na+]>ClCCl>[C:5]([O:8][C:9]1[C:14]([C:15]([CH3:17])([CH3:16])[CH3:18])=[CH:13][C:12]2[O:19][C:21]([CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])([CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:20][C:11]=2[C:10]=1[C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 516892Sodium BicarbonateHCID 11070377HCID 11070377, compound

Product 1

HCID 111128205-Acetoxy-2,2-diisoamyl-4,6-di-tert-butyl-2,3-dihydrobenzofuranYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BF3 etherate (4.7 ml) was added dropwise to a solution of 4-acetoxy-3,5-di-tert-butyl-2-(2,2-diisoamyl-1-hydroxyethyl)-phenol (17.0 g) in dichloromethane under cooling with ice under a nitrogen atmosphere. After stirring the mixture overnight at room temperature, a saturated aqueous solution of sodium hydrogen carbonate was added. After separating the organic layer, the aqueous layer was subjected to extraction with dichloromethane. The extract was combined with the organic layer, washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled off to afford 5-acetoxy-2,2-diisoamyl-4,6-di-tert-butyl-2,3-dihydrobenzofuran [15.5 g (yield, 95%)] as a colorless oil.

Workup

  1. temperatureunder cooling with ice under a nitrogen atmosphere
  2. customAfter separating the organic layer
  3. extractionthe aqueous layer was subjected to extraction with dichloromethane
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-4469e1f861a148b082a4023a7f944f3e
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

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