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

HRID 1452353Notes

Reaction equation

HRID 1452353 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

Triethylsilane (2.8 ml) was added to 4-tert-butyl-5-hydroxy-2-octylbenzofuran (300 mg, 1.0 mmol) and, then, trifluoroacetic acid (1.4 ml) was added dropwise under ice cooling. The mixture was stirred first at 0° C. for 15 min, then at room temperature for 1 h. Thereafter, the mixture was poured into ice water and subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (chloroform) to afford 4-tert-butyl-5-hydroxy-2-octyl-2,3-dihydrobenzofuran [252 mg (yield, 83%)] as a colorless oil.

Workup

  1. waitat room temperature for 1 h
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel chromatography (chloroform)

Sources & evidence

ORD record
ord-2be4ff0376ec441d849a617eb1a7bbd5
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

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