Boron trifluoride etherate → HCID 23442893, compound

HRID 2119718Notes

Reaction equation

HRID 2119718 reaction equation
[C:1]([C:5]1[C:6]([O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:7][C:8]([CH2:12][CH:13]=[CH2:14])=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([C:5]1[C:6]([O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:7][C:8]2[CH2:12][CH:13]([CH3:14])[O:11][C:9]=2[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 23442896HCID 23442896, compound

Product 1

HCID 23442893HCID 23442893, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.50 g of 5-t-butyl-4-trimethylacetoxy-2-(2-propenyl)phenol was dissolved in 30 ml of dichloromethane, 30 ml of boron trifluoride etherate was added, and the solution was stirred at room temperature under a nitrogen stream. The solution was further refluxed for 30 minutes, and the reaction solution was poured into a saturated aqueous sodium bicarbonate solution and extracted with n-hexane. The organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 0.5%-1% ethyl acetate) to give 0.15 g of 6-t-butyl-2-mehtyl-5-trimethylacetoxy-2,3-dihydrobenzofuran as a colorless solid (yield 30%).

Workup

  1. temperatureThe solution was further refluxed for 30 minutes
  2. extractionextracted with n-hexane
  3. washThe organic layers were washed with 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 0.5%-1% ethyl acetate)

Sources & evidence

ORD record
ord-738525a01dd343ac9f75aa1118f22d1d
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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