Water → HCID 23114734, compound

HRID 2080480Notes

Reaction equation

HRID 2080480 reaction equation
O1CCCC1.[Si]([O:13][CH2:14][C:15]1[CH:20]=[C:19]([CH:21]([S:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[F:29])[C:18]([CH3:38])=[CH:17][N:16]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>CCCCCC>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([S:30][CH:21]([C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[F:29])[C:19]2[C:18]([CH3:38])=[CH:17][N:16]=[C:15]([CH2:14][OH:13])[CH:20]=2)=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 23114866HCID 23114866, compound

Product 1

HCID 23114734HCID 23114734, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a tetrahydrofuran solution (3 ml) of 2-[(t-butyldimethylsilyloxy)methyl]-4-[(4-chlorophenylthio)(2,5-difluorophenyl)methyl]-5-methylpyridine (200 mg, 0.395 mmol) was added tetrabutylammonium fluoride (a 1.0M tetrahydrofuran solution, 593 μl, 0.593 mmol). The resulting mixture was stirred for 20 minutes. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated under reduced pressure to give the title compound (150 mg, 0.384 mmol, 97%) as a colorless oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. concentrationethyl acetate=3:1 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8214d9a10cc24f22afd1d1db1feacf10
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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