Tetrabutylammonium Fluoride → HCID 59750820, compound

HRID 748677Notes

Reaction equation

HRID 748677 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:36]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=1[F:43])([CH2:24][CH2:25][CH2:26][CH2:27][O:28][Si](C(C)(C)C)(C)C)[S:14]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)C>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([S:14]([C:13]([C:36]2[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=2[F:43])([CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[CH2:24][CH2:25][CH2:26][CH2:27][OH:28])(=[O:16])=[O:15])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 230287082-[5-(t-Butyldimethylsilyloxy)-1-[4-(t-butyldimethylsilyloxy)butyl]-1-(4-chlorophenylsulfonyl)pentyl]-1,4-difluorobenzene

Product 1

HCID 59750820HCID 59750820, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-[5-(t-butyldimethylsilyloxy)-1-[4-(t-butyldimethylsilyloxy)butyl]-1-(4-chlorophenylsulfonyl)pentyl]-1,4-difluorobenzene (158 mg, 0.234 mmol) in tetrahydrofuran (4 ml) was added tetrabutylammonium fluoride (a 1M tetrahydrofuran solution, 0.702 ml, 0.702 mmol). The resulting mixture was stirred at room temperature for 24 hours. After concentration of the reaction mixture, the residue was dissolved in diethyl ether, followed by successive washing with water and brine, drying over MgSO4, and concentration. The residue thus obtained was purified by medium-pressure chromatography on a silica gel column (5% methanol-methylene chloride) to yield a colorless solid. The resulting solid was recrystallized from ethyl acetate-hexane, whereby the title compound (97.0 mg, 93%) was obtained as a colorless solid.

Workup

  1. washby successive washing with water and brine
  2. dry with materialdrying over MgSO4, and concentration
  3. customThe residue thus obtained
  4. customwas purified by medium-pressure chromatography on a silica gel column (5% methanol-methylene chloride)
  5. customto yield a colorless solid
  6. customThe resulting solid was recrystallized from ethyl acetate-hexane, whereby the title compound (97.0 mg, 93%)
  7. customwas obtained as a colorless solid

Sources & evidence

ORD record
ord-109177de2fe44361b915926d8738c9b8
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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