Tetrabutylammonium Fluoride Trihydrate → HCID 58941346, compound

HRID 747627Notes

Reaction equation

HRID 747627 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][N:10]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[CH2:31][C:32]1[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=1[F:39])[S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)(=[O:13])=[O:12])(C)(C)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([N:10]([CH2:9][CH2:8][CH2:7][OH:6])[S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)(=[O:13])=[O:12])=[C:25]([CH2:31][C:32]2[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=2[F:39])[CH:26]=1

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 68572431HCID 68572431, compound

Product 1

HCID 58941346HCID 58941346, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 8 g of N-(3-{[tertbutyl(dimethyl)silyl]oxy}propyl)-N-[4-chloro-2-(2,6-difluorobenzyl)phenyl]-3,4-dimethoxybenzenesulfonamide in 80 ml of tetrahydrofuran at 0° C. are added 2.98 g of tetrabutylammonium fluoride trihydrate. After 40 minutes at 25° C., the reaction medium is concentrated and then chromatographed on a column of silica gel, eluting with dichloromethane, to give 3.28 g of the expected product.

Workup

  1. concentrationthe reaction medium is concentrated
  2. customchromatographed on a column of silica gel
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-209468437142480d9ca649e44b1d9826
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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