Water → HCID 23114377, compound

HRID 2376550Notes

Reaction equation

HRID 2376550 reaction equation
O[C:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[C:6]2[CH:7]=[C:8]([NH:13][C:14](=[O:20])[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:9]([CH3:12])=[C:10]([CH3:11])[C:5]=2[O:4][C:3]1([CH3:22])[CH3:21].C([SiH](CC)CC)C.O>FC(F)(F)C(O)=O>[CH3:17][C:16]([CH3:19])([CH3:18])[CH2:15][C:14]([NH:13][C:8]1[C:9]([CH3:12])=[C:10]([CH3:11])[C:5]2[O:4][C:3]([CH3:21])([CH3:22])[CH:2]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])[C:6]=2[CH:7]=1)=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 12052TriethylsilaneHCID 23114188HCID 23114188, compound

Product 1

HCID 23114377HCID 23114377, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of N-(3-hydroxy-2,2,6,7-tetramethyl-3-(2-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (120 mg, 0.3 mmol) obtained in Example 242 in trifluoroacetic acid (2 mL) was added triethylsilane (71 mg, 0.6 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. The reaction solution was added to water and the product was extracted with ethyl acetate. The organic layer was washed with an aqueous 1 N sodium hydroxide solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2) and recrystallized from ethyl acetate-hexane to obtain 93 mg (yield: 79%) of the title compound. Melting point: 161-162° C.

Workup

  1. temperaturecooling
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous 1 N sodium hydroxide solution, water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)
  7. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1077b185812a4f25ad947fc5c1d7ec93
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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