Water → HCID 23113957, compound

HRID 2376582Notes

Reaction equation

HRID 2376582 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][C:4]([NH:6][C:7]1[C:8]([CH3:20])=[CH:9][C:10]2[O:14][C:13]([CH3:16])([CH3:15])[CH:12](O)[C:11]=2[C:18]=1[CH3:19])=[O:5].C([SiH](CC)CC)C.O>FC(F)(F)C(O)=O>[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][C:4]([NH:6][C:7]1[C:8]([CH3:20])=[CH:9][C:10]2[O:14][C:13]([CH3:15])([CH3:16])[CH2:12][C:11]=2[C:18]=1[CH3:19])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 12052TriethylsilaneHCID 23113898HCID 23113898, compound

Product 1

HCID 23113957HCID 23113957, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a mixed solution of 3,3-dimethyl-N-(3-hydroxy-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)butanamide (2.0 g, 6.55 mmol) obtained in Example 338 in trifluoroacetic acid (3 mL) was added dropwise with ice-cooling triethylsilane (2.09 g, 13.10 mmol). The reaction solution was warmed to room temperature and stirred for 30 minutes. Water was added to the reaction solution and the product was extracted with ethyl acetate. The combined organic layers were washed with an aqueous 1 N sodium hydroxide solution and an aqueous saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure to obtain 1.75 g (yield: 92%) of the title compound. Melting point: 181-182° C. (THF-hexane).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe combined organic layers were washed with an aqueous 1 N sodium hydroxide solution
  3. dry with materialan aqueous saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3b4df73d224446fb4d560ba63e27b40
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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