Water → HCID 59477768, compound

HRID 1516577Notes

Reaction equation

HRID 1516577 reaction equation
[H-].[Na+].[Si:3]([O:20][CH2:21][CH:22]=[CH:23][C:24]#[N:25])([C:16]([CH3:19])([CH3:18])[CH3:17])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(C)C=CC(S([CH2:35][N+:36]#[C-])(=O)=O)=CC=1.O.[CH2:40](OCC)C>CS(C)=O>[Si:3]([O:20][CH2:21][C:22]1[C:23]([C:35]#[N:36])=[CH:24][NH:25][CH:40]=1)([C:16]([CH3:18])([CH3:19])[CH3:17])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 962WaterHCID 3283Diethyl Ether2×HCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanideHCID 68504321HCID 68504321, compound

Product 1

HCID 59477768HCID 59477768, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.12 g) in diethyl ether (5 mL) were added a solution of 4-(tert-butyldiphenylsilanyloxy)-buta-2-ennitrile (0.81 g) and p-toluensulfonylmethylisocyanide (0.49 g) in diethyl ether (5 mL) and dimethylsulfoxide (5 mL). After stirring at room temperature for 5 hours, to this reaction mixture was added water and this reaction mixture was extracted with ethyl acetate. This organic layer was washed with brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=60/40-39/61) to give the title compound (0.50 g).

Workup

  1. extractionthis reaction mixture was extracted with ethyl acetate
  2. washThis organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=60/40-39/61)

Sources & evidence

ORD record
ord-a36e63237d3a4f568ed6f77769592c7b
Source dataset
uspto-grants-2012_07
Patent number
US08227500B2

Reaction notes

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