Trifluoroacetic acid → 4-Tert-butyl-5-hydroxy-2-octyl-2,3-dihydrobenzofuran

HRID 2119691Notes

Reaction equation

HRID 2119691 reaction equation
C([SiH](CC)CC)C.[C:8]([C:12]1[C:17]2[CH:18]=[C:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[O:20][C:16]=2[CH:15]=[CH:14][C:13]=1[OH:29])([CH3:11])([CH3:10])[CH3:9].FC(F)(F)C(O)=O>>[C:8]([C:12]1[C:17]2[CH2:18][CH:19]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[O:20][C:16]=2[CH:15]=[CH:14][C:13]=1[OH:29])([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 234428644-Tert-butyl-5-hydroxy-2-octylbenzofuran

Product 1

HCID 234428864-Tert-butyl-5-hydroxy-2-octyl-2,3-dihydrobenzofuranYield 83%

Conditions

Temperature
0 °C

Procedure

2.8 ml of triethylsilane was added to 0.3 g of 4-t-butyl-5-hydroxy-2-n-octylbenzofuran and then 1.4 ml of trifluoroacetic acid was added dropwise to this mixture under ice-cooling. After stirring at 0° C. for 15 minutes and then at room temperature for 1 hour, 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 chloroform) to give 0.25 g of 4-t-butyl-5-hydroxy-2-n-octyl-2,3-dihydrobenzofuran as a colorless oil (yield 83%).

Workup

  1. temperaturecooling
  2. waitat room temperature for 1 hour
  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 chloroform)

Sources & evidence

ORD record
ord-5319200ebe3d45fe8722b08f1a66f77f
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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