Sodium hydride → HCID 70028981, compound

HRID 1370774Notes

Reaction equation

HRID 1370774 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH:13]=[CH:14][C:15]#[N:16].[I-].[CH3:18][S+](C)(C)=O.[H-].[Na+]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C@@H:13]1[CH2:18][C@H:14]1[C:15]#[N:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 69959769HCID 69959769, compound

Product 1

HCID 70028981HCID 70028981, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

5 g (23.9 mmol) of the compound obtained in Step A dissolved in 50 ml of DMSO are added dropwise to the ylid formed starting from 7.9 g (1.5 eq) of trimethylsulphoxonium iodide and 1.15 g (1.2 eq) of NaH (60% suspension in oil) in 20 ml of DMSO. The title compound is obtained in the form of an oil and is purified by chromatography over silica gel (eluant: CH2Cl2/i-PrOH 98/2).

Workup

  1. additionare added dropwise to the ylid
  2. customformed

Sources & evidence

ORD record
ord-66a28fee5c274339a198f2c3a83917a4
Source dataset
uspto-grants-2003_06
Patent number
US06583319B1

Reaction notes

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