Trifluoroacetic acid → HCID 23442892, compound

HRID 2186259Notes

Reaction equation

HRID 2186259 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:12]1[C:17]2[CH:18]=[C:19]([CH3:21])[O:20][C:16]=2[CH:15]=[CH:14][C:13]=1[OH:22])([CH3:11])([CH3:10])[CH3:9]>C([SiH](CC)CC)C>[C:8]([C:12]1[C:17]2[CH2:18][CH:19]([CH3:21])[O:20][C:16]=2[CH:15]=[CH:14][C:13]=1[OH:22])([CH3:11])([CH3:9])[CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 234428664-t-Butyl-5-hydroxy-2-methylbenzofuran

Product 1

HCID 23442892HCID 23442892, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 12052TriethylsilaneSolvent

Conditions

Temperature
0 °C

Procedure

Under ice-cooling, 1.4 ml of trifluoroacetic acid was added dropwise to 0.25 g of 4-t-butyl-5-hydroxy-2-methylbenzofuran in 2.8 ml of triethylsilane. After stirring at 0° C. for 15 minutes and then at room temperature for 18 hours, the mixture was poured into ice water and extracted with ethyl acetate. The extracted layers were washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 20% ethyl acetate) to give 0.18 g of 4-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran as a white crystal (yield 74%).

Workup

  1. temperatureUnder ice-cooling
  2. waitat room temperature for 18 hours
  3. extractionextracted with ethyl acetate
  4. washThe extracted layers were washed with a saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 20% ethyl acetate)

Sources & evidence

ORD record
ord-a2cbb3ed80054fdd9cbdaffd6d94eb32
Source dataset
uspto-grants-2002_06
Patent number
US06403639B1

Reaction notes

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