| Identification | Back Directory | [Name]
TERT-BUTYL TRIMETHYLSILYLACETATE | [CAS]
41108-81-0 | [Synonyms]
Einecs 255-222-2
t-Butyl Trimethylsilylacetate
TERT-BUTYL TRIMETHYLSILYLACETATE
tert-butyl 2-trimethylsilylacetate
1,1-dimethylethyl trimethylsilylacetate
(Trimethylsilyl)acetic acid 1,1-dimethylethyl ester
Acetic acid, 2-(trimethylsilyl)-, 1,1-dimethylethyl ester | [EINECS(EC#)]
255-222-2 | [Molecular Formula]
C9H20O2Si | [MDL Number]
MFCD00042855 | [MOL File]
41108-81-0.mol | [Molecular Weight]
188.34 |
| Hazard Information | Back Directory | [Physical properties]
air stable, colorless liquid; bp 67°C/13 mmHg;
n20
D 1.4184; 1H NMR (CDCl3, 90 MHz) 0.13 (s, 9H), 1.45
(s, 9H), 1.80 (s, 2H); IR 1710 cm?1. | [Uses]
t-Butyl Trimethylsilylacetate is used to prepare lithium enolates which can be alkylated;can
be alkenated with aldehydes and ketones;can be acylated;can
be reacted with Group 14 halides.
Most applications require initial formation
of the enolate (1) (eq 1), which is obtained as a white solid suspended
in THF, stable indefinitely at ?78°C. | [Preparation]
an advantage of t-butyl trimethylsilylacetate
over its methyl and ethyl ester analogs is that it can be prepared
by C-silylation of the lithium enolate of t-butyl acetate at
?78°C in THF (85–90% yield). Under the same conditions the
enolates of methyl and ethyl acetate give primarily O-silylated
products.The reagent has also been prepared by a rapid boron
trifluoride etherate catalyzed reaction of trimethylsilylketene
with t-butyl alcohol. |
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