Trifluoroacetic acid → HCID 15391748, compound

HRID 1900527Notes

Reaction equation

HRID 1900527 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]=[C:14]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:13]=1[OH:33])([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]=[C:14]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:13]=1[OH:33])([CH3:10])([CH3:11])[CH3:9]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 18433161HCID 18433161, compound

Product 1

HCID 15391748HCID 15391748, compoundYield 27.1%

Conditions

Temperature
0 °C

Procedure

Triethylsilane (17.4 ml) was added to 4,6-di-tert-butyl-5-hydroxy-2-octylbenzofuran (2.2 g) and trifluoroacetic acid (8.7 ml) was added dropwise to the mixture under cooling with ice. After stirring at 0° C. for 1 h, 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 (n-hexane) to afford 4,6-di-tert-butyl-5-hydroxy-2-octyl-2,3-dihydrobenzofuran [0.6 g (yield, 27%)].

Workup

  1. additionwas added dropwise to the mixture
  2. temperatureunder cooling with ice
  3. extractionsubjected to extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel chromatography (n-hexane)

Sources & evidence

ORD record
ord-21eb7042a1874db885e19a18b0605a06
Source dataset
uspto-grants-1996_11
Patent number
US05574178

Reaction notes

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