Water → HCID 59477768, compound

HRID 570830Notes

Reaction equation

HRID 570830 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-c31fb4a13c584bd3a5781a0ebd8d3a81
Source dataset
uspto-grants-2015_05
Patent number
US09023882B2

Reaction notes

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