1-METHOXY-1-TRIMETHYLSILYLOXYPROPENE Chemical Properties

Boiling point:

52 °C / 27mmHg

Density 

0.87

refractive index 

1.4130-1.4160

storage temp. 

0-10°C

form 

clear liquid

color 

Colorless to Almost colorless

Specific Gravity

0.87

CAS DataBase Reference

34880-70-1

Safety Information

RIDADR 

1993

HazardClass 

3

PackingGroup 

III

HS Code 

2931900090

1-METHOXY-1-TRIMETHYLSILYLOXYPROPENE Usage And Synthesis

Uses

1-Methoxy-1-(trimethylsilyloxy)propene is used to reactive nucleophile in Mukaiyama-type aldol reactions with aldehydes, imines, acetals, dialkoxycarbenium ions, and orthoesters; Michael-type additions to α,β-unsaturated carbonyl compounds; substitution reactions with allylic alcohols and esters; acylations; aminations; hydroxylations; and pericyclic reactions; silylating agent.

Preparation

since the first preparation of a ketene trialkylsilyl acetal by Petrov in 1959 by the reaction of triethylsilane and methyl acrylate, several alternative pathways have been explored. Ainsworth and coworkers prepared 1-methoxy-1-(trimethylsilyloxy)propene in 90% yield by deprotonation of methyl propionate with Lithium Diisopropylamide at -78 °C followed by addition of Chlorotrimethylsilane. Reaction of the lithium enolate of methyl acetate with TMS-Cl provides 65% O-silylated and 35% C-silylated products (eq 1). Substitution on the alcohol portion of the ester favors C-silylation while substitution on the α-carbon favors O-silylation. An increase in the steric bulk of the silylating agent (e.g. use of t-Butyldimethylchlorosilane) results in significantly more O-silylation.

storage

1-Methoxy-1-(trimethylsilyloxy)propene is easily hydrolyzed and oxidized by exposure to air. Storage is possible in sealed tubes at rt. Use in a fume hood.

1-METHOXY-1-TRIMETHYLSILYLOXYPROPENE(34880-70-1)Related Product Information

• tert-Butyldimethylsilyl chloride
• 1-(2-TRIMETHYLSILOXYETHOXY)-1-TRIMETHYLSILOXY-2-METHYLPROPENE
• (1E)-1-tert-Butoxy-1-(trimethylsilyloxy)propene
• 1-METHOXY-1-TRIMETHYLSILYLOXYPROPENE
• 3,4-DIHYDRO-6-(TRIMETHYLSILYLOXY)-2H-PYRAN
• DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL
• 3,4-DIHYDRO-6-[(TERT-BUTYL)DIMETHYL SILYLOXY]-2H-PYRAN