Water → HCID 23113918, compound

HRID 2376342Notes

Reaction equation

HRID 2376342 reaction equation
[CH2:1]([C:3]1(CCC)[C:7]2[C:8]([CH3:23])=[CH:9][C:10]([CH3:22])=[C:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[C:6]=2[O:5][CH2:4]1)[CH3:2].C([SiH](CC)CC)C.O>FC(F)(F)C(O)=O>[CH2:1]([CH:3]1[C:7]2[C:8]([CH3:23])=[CH:9][C:10]([CH3:22])=[C:11]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([CH:19]([CH3:20])[CH3:21])=[CH:17][CH:18]=3)[C:6]=2[O:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 12052TriethylsilaneHCID 23114227HCID 23114227, compound

Product 1

HCID 23113918HCID 23113918, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a mixed solution of 3-ethyl-7-(4-isopropylbenzyl)-4,6-dimethyl-3-propyl-1-benzofuran obtained in Reference Example 183 (941 mg, 2.94 mmol) in trifluoroacetic acid (5 mL) was added dropwise triethylsilane (0.94 mL, 5.87 mmol), and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution, which was extracted with ethyl acetate, and then the organic layer was washed with a saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 940 mg (yield 99%) of the title compound. Oily matter.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washthe organic layer was washed with a saturated sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-fc6f2762a53541e29714b0bd9fbe492a
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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