Propose an efficient synthesis for the given transformation. HO + En OMe This transformation can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A D E t-BUOK 1) &:2) 1) &: 2) H30* 1) NaOMe; 2) H2, Lindlar's cat. F G H 1) HC=CNa; 2) NaH МСРВА Br2, hv HBr (xs), heat (RCO3H) K M N DMP or PCC MEOH, H2SO4 H2SO4, H2O, H9SO4 1) R2BH; 2) H2O2. NaOH

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter24: Carboxylic Acids & Derivatives
Section: Chapter Questions
Problem 16CTQ
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Propose an efficient synthesis for the given transformation.
OH
En
"OMe
This transformation can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in
the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution,
provide just one answer.
A
D
E
1) &: 2)
1) &:2) H,0*
t-BUOK
1) NaOMe; 2)
H2, Lindlar's cat.
H3O+
H3O*
F
G
H
1) НCЕCNa; 2)
NaH
МСРВА
Br2, hv
HBr (xs), heat
H3O*
(RCO3H)
K
L
M
H2SO4, H20,
HgSO4
MeONa
DMP or PCC
МеОн, Н2SO4
1) R2BH; 2) H2O2,
NAOH
Transcribed Image Text:Propose an efficient synthesis for the given transformation. OH En "OMe This transformation can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A D E 1) &: 2) 1) &:2) H,0* t-BUOK 1) NaOMe; 2) H2, Lindlar's cat. H3O+ H3O* F G H 1) НCЕCNa; 2) NaH МСРВА Br2, hv HBr (xs), heat H3O* (RCO3H) K L M H2SO4, H20, HgSO4 MeONa DMP or PCC МеОн, Н2SO4 1) R2BH; 2) H2O2, NAOH
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