Tetrahydrofuran → HCID 23114639, compound

HRID 2080370Notes

Reaction equation

HRID 2080370 reaction equation
O1CCCC1.[Si]([O:23][CH2:24][C:25]1[CH:26]=[C:27]([F:41])[C:28]([CH:31]([C:33]2[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=2[F:40])[OH:32])=[N:29][CH:30]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC>C(OCC)(=O)C>[F:40][C:34]1[CH:35]=[CH:36][C:37]([F:39])=[CH:38][C:33]=1[CH:31]([C:28]1[C:27]([F:41])=[CH:26][C:25]([CH2:24][OH:23])=[CH:30][N:29]=1)[OH:32]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8058HexaneHCID 2724141Tetrabutylammonium FluorideHCID 23114720HCID 23114720, compound

Product 1

HCID 23114639HCID 23114639, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran (7 ml) solution of [5-(t-butyldiphenylsilyloxymethyl)-3-fluoropyridin-2-yl](2,5-difluorophenyl)methanol (853 mg, 1.68 mmol) was added a tetrahydrofuran solution (1.04 ml, 1.04 mmol) of tetrabutylammonium fluoride. The mixture was stirred at room temperature for 5 hours. After the reaction mixture was concentrated under reduced pressure, the residue thus obtained was dissolved in ethyl acetate. The resulting solution was washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate and then, filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography. The fraction obtained from the hexane:ethyl acetate=1:1 eluate was concentrated under reduced pressure to give the title compound (413 mg, 1.53 mmol, 91%) as a white solid.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. customthe residue thus obtained
  3. washThe resulting solution was washed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe residue thus obtained
  8. concentrationethyl acetate=1:1 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-627a7d28f5344bfb8aa7031c90455dc1
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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