HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Tetrabutylammonium Fluoride → 5-(4-Chlorophenylsulfonyl)-5-(2,5-difluorophenyl)-1-hexanol

HRID 748675
Notes
Print preview

Reaction equation

HRID 748675 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([C:43]1[CH:48]=[C:47]([F:49])[CH:46]=[CH:45][C:44]=1[F:50])([S:33]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)(=[O:35])=[O:34])[CH3:32])(C(C)(C)C)(C)C>O1CCCC1.C(OCC)C>[Cl:42][C:39]1[CH:38]=[CH:37][C:36]([S:33]([C:31]([C:43]2[CH:48]=[C:47]([F:49])[CH:46]=[CH:45][C:44]=2[F:50])([CH3:32])[CH2:30][CH2:29][CH2:28][CH2:27][OH:26])(=[O:35])=[O:34])=[CH:41][CH:40]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 597507792-[5-(t-Butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-1-methylpentyl]-1,4-difluorobenzene

Product 1

HCID 230287835-(4-Chlorophenylsulfonyl)-5-(2,5-difluorophenyl)-1-hexanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028Tetrahydrofuran
Solvent
2×

Procedure

After addition of tetrabutylammonium fluoride (a 1M tetrahydrofuran solution, 0.978 ml, 0.978 mmol) to a solution of 2-[5-(t-butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-1-methylpentyl]-1,4-difluorobenzene (164 mg, 0.326 mmol) in tetrahydrofuran (4 ml), the mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with diethyl ether, washed successively with saturated ammonium chloride, water and brine, dried over MgSO4, and then concentrated. The residue thus obtained was purified by medium-pressure chromatography on a silica gel column (50% ethyl acetate-hexane), whereby the title compound (122 mg, 96%) was obtained as a colorless oil.

Workup

  1. washwashed successively with saturated ammonium chloride, water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue thus obtained
  5. customwas purified by medium-pressure chromatography on a silica gel column (50% ethyl acetate-hexane), whereby the title compound (122 mg, 96%)
  6. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-430c4b000ac5451b91aff47ae69e262e
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07399775B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes