Please provide appropriate reagents to achieve the conversion of B into α,ẞ-unsaturated ester C over several steps.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter17: Alcohols And Phenols
Section17.SE: Something Extra
Problem 60AP: Benzvl chloride can be converted into benzaldehvde by treatment with nitromethane and base. The...
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Please provide appropriate reagents to achieve the conversion of B into α,ẞ-unsaturated ester C over several steps.
CO₂CH3
CO₂CH3
H
t-BuO.
H
H
LIHMDS, t-BuO
THF, -78 °C;
H
H
t-BuO.
?
H
H
N
H
OTBS
H3CO
CN
OTBS
A
B (92%)
OTBS
с
In the first step we can use
Then we can use¦
The final stage is
Strong base, heat
MsCl, Et3N
12, ОН-
(both in excess)
1) LDA, THF
2) CHẠI
H
Pt, heat
NaBH4, H3O+
Transcribed Image Text:Please provide appropriate reagents to achieve the conversion of B into α,ẞ-unsaturated ester C over several steps. CO₂CH3 CO₂CH3 H t-BuO. H H LIHMDS, t-BuO THF, -78 °C; H H t-BuO. ? H H N H OTBS H3CO CN OTBS A B (92%) OTBS с In the first step we can use Then we can use¦ The final stage is Strong base, heat MsCl, Et3N 12, ОН- (both in excess) 1) LDA, THF 2) CHẠI H Pt, heat NaBH4, H3O+
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