Triethylsilane → Methyl 3,5-diallyloxy-2-ethylphenylacetate

HRID 499870Notes

Reaction equation

HRID 499870 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH2:11][CH:12]=[CH2:13])=[CH:8][C:7]([O:14][CH2:15][CH:16]=[CH2:17])=[CH:6][C:5]=1[CH2:18][C:19]([O:21][CH3:22])=[O:20])(=O)[CH3:2].C([SiH](CC)CC)C.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[CH2:11]([O:10][C:9]1[C:4]([CH2:1][CH3:2])=[C:5]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:6]=[C:7]([O:14][CH2:15][CH:16]=[CH2:17])[CH:8]=1)[CH:12]=[CH2:13]

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 68421776Methyl 2-acetyl-3,5-diallyloxyphenylacetate

Product 1

HCID 23116370Methyl 3,5-diallyloxy-2-ethylphenylacetateYield 62%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Methyl 2-acetyl-3,5-diallyloxyphenylacetate (1.1 g, 3.7 mmol) obtained in Example 5, Step 2 was dissolved in trifluoroacetic acid (5.0 mL), and triethylsilane (1.2 mL, 7.5 mmol) was added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was gradually added to a saturated aqueous solution of sodium hydrogencarbonate for neutralization, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate/hexane=1/4) to obtain methyl 3,5-diallyloxy-2-ethylphenylacetate (0.66 g, 62%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-562cd47e77bc434a8d1a9e45b407dce0
Source dataset
uspto-grants-2010_08
Patent number
US07767693B2

Reaction notes

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