Water → HCID 59533958, compound

HRID 1697276Notes

Reaction equation

HRID 1697276 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.O.O.O.[F-].[Cl:22][C:23]1[CH:24]=[C:25]([S:30]([N:33]([CH2:50][P:51](=[O:58])([O:55][CH2:56][CH3:57])[O:52][CH2:53][CH3:54])[C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=[CH:36][C:35]=2[C:44]#[C:45][Si](C)(C)C)(=[O:32])=[O:31])[CH:26]=[C:27]([Cl:29])[CH:28]=1.O>O1CCCC1>[Cl:22][C:23]1[CH:24]=[C:25]([S:30]([N:33]([CH2:50][P:51](=[O:58])([O:52][CH2:53][CH3:54])[O:55][CH2:56][CH3:57])[C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=[CH:36][C:35]=2[C:44]#[CH:45])(=[O:31])=[O:32])[CH:26]=[C:27]([Cl:29])[CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 59534089HCID 59534089, compound

Product 1

HCID 59533958HCID 59533958, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

115 mg tetrabutylammonium fluoridetrihydrate are added to 155 mg diethyl {[(3,5-dichloro-phenylsulphonyl)-(2-trimethylsilanylethynyl-naphthalen-1-yl)-amino]-methyl}-phosphonate in 4 ml of tetrahydrofuran at ambient temperature. The reaction mixture is stirred for 15 minutes at ambient temperature, then it is mixed with water and extracted with ethyl acetate. The combined extracts are dried on magnesium sulphate and evaporated down. The flask residue is chromatographed through a silica gel column with cyclohexane/ethyl acetate (50:50) as eluant.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe combined extracts are dried on magnesium sulphate
  3. customevaporated down
  4. customThe flask residue is chromatographed through a silica gel column with cyclohexane/ethyl acetate (50:50) as eluant

Sources & evidence

ORD record
ord-b4d64d953eff458096ea1cd15fd0f278
Source dataset
uspto-grants-2012_04
Patent number
US08163911B2

Reaction notes

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