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Preparation of Methyl 2‐[Bis(trimethylsiloxy)phosphoryl]‐3,3,3‐trifluoro‐2– (trimethylsiloxy)propionate and Some Derivatives‐Molecular Structure of Methyl 2‐[Bis(trimethylsiloxy)phosphoryl]‐3,3,3‐trifluoro‐2‐hydroxypropionate
Author(s) -
Schoth RalphMatthias,
Lork Enno,
Seifert Frank Uwe,
Breuer Eli,
Röschenthaler GerdVolker
Publication year - 1997
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19971300222
Subject(s) - chemistry , propionate , phosphonate , trimethylsilyl , hydrolysis , tris , silylation , medicinal chemistry , propionates , stereochemistry , organic chemistry , catalysis , biochemistry
Methyl trifluoropyruvate ( 1 ) and tris(trimethylsilyl) phosphite ( 3 ) reacted to give methyl 2‐[bis(trimethylsiloxy)phosphoryl]‐ 3,3,3‐trifluoro‐2‐(trimethylsiloxy) propionate ( 4 ). Partial hydrolysis furnished propionate 6 , the molecular structure of which was obtained in the solid state. Attempted trimethylsilylation of the methylcarboxylato group in 4 using iodotrimethylsilane caused the formation of bis(trimethylsily1) [(2,2‐ difluoro‐ 1 ‐trimethylsiloxy)ethenyl]phosphonate ( 8 ). For comparison, methyl pyruvate ( 2 ) and 3 gave methyl 2‐[bis(trimethylsiloxy)phosphoryl]‐2‐(trimethylsiloxy)propionate ( 5 ).