Sodium methylsulfinylmethide

Carbohydroxy-n-butyl)triphenylphosphonium bromide Sodium methylsulfinylmethide... 

Shemyakin and co-workers, investigating the synthesis of tetracycline antibiotics, found sodium methylsulfinylmethide more satisfactory than sodium hydride, sodium amide, or sodium dispersion for the cyclization of (3) to (4). 

Gardner and co-workers found sodium methylsulfinylmethide a very effective... 

Carey s procedure. The salt is trimethylsulfonium iodide (I), the base is a solution of sodium methylsulfinylmethide (2), prepared by heating a mixture of powdered sodium hydride (0.1 ra.) with excess DMSO with stirring under nitrogen at 75 ... 

Roberts and Whiting developed a method for effecting the anhydrous hydrolysis of esters and nitriles in DMSO. A solution of sodium methylsulfinylmethide is prepared from sodium hydride and DMSO and titrated with a solution of an appropriate amount of water in DMSO, using triphenylmethane as indicator. This produces a fine suspension of sodium hydroxide which hydrolyzes ethyl benzoate very rapidly at room temperature. As compared with reactions in hydroxylic solvents, rates are enhanced by a factor of 10 -10 . Benzonitrile is hydrolyzed to benzamide. Methyl and ethyl mesitoates are hydrolyzed readily at 25°. 

Dimethyl sulfoxide-derived reagent (a). Sodium methylsulfinylmethide, now generally known as Dimsylsodium, [ ch3s(o )=ch2 <—> CH3(s=0)-C H2]Na+ [1, 311, after line... 

Sodium hydroxide, 158 Sodium hypobromite, 383-384 Sodium hypochlorite, 67 Sodium iodide, 166, 384, 461 Sodium isopropoxide, 385 Sodium-lead alloy, 385 Sodium methoxide, 223, 385-386, 418 Sodium 2-methyl-2-butoxide, 138, 386 Sodium methyl phosphorazidate, 386 Sodium methylsulfinylmethide, 130, 166-169, 284... 

ALKYNES Dimethyl sulfoxide-derived reagent (a). Sodium methylsulfinylmethide. 

X-Hydroxy-1 lot, 15triphenyl-phosphonium bromide in a dry nitrogen atmosphere in 6.0 ml dry dimethyl sulfoxide wasadded 3.24 ml (6.5 mmols) of a 2.0M solution of sodium methylsulfinylmethide in dimethyl sulfoxide. To this red ylide solution was added dropwise a solution of 613 mg (1.29 mmols) 2-[50 -hydroxy-30 -(tetrahydropyran-2-yloxy)-2/3-(30 -tetrahydropyran-2-yloxy-4-phenoxy-trans-1-buten-1-yl)cyclopent-10 -yll acetaldehyde, 7-hemiacetal in 5.0 ml dry dimethyl sulfoxide over a period of 20 minutes. 

Obtained by reaction of ethyl 2,4-dihy-droxy-6-methyl-benzoate with sodium methylsulfinylmethide [5586] according to [5587]. 

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