During the synthesis of the antiasthmatic drug montelukast (Singulair), a silyl ether protecting group is used to mask the reactivity of an OH group. The silyl group chosen is the tert-butyldimethylsilyl (TBS) group. Draw the product of the following transforma- tion, assuming the TBS-Cl reagent reacts only once with the starting material. Briefly explain your answer. CH3 НО H3C-C-CH3 H3C-Si-CH3 CH3 H3C OH Cl, CI Imidazole (base) DMF/CH,Cl,

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
Question
During the synthesis of the antiasthmatic drug montelukast (Singulair), a silyl ether
protecting group is used to mask the reactivity of an OH group. The silyl group chosen is
the tert-butyldimethylsilyl (TBS) group. Draw the product of the following transforma-
tion, assuming the TBS-Cl reagent reacts only once with the starting material. Briefly
explain your answer.
CH3
НО
H3C-C-CH3
H3C-Si-CH3
CH3
H3C
OH
Cl,
CI
Imidazole (base)
DMF/CH,Cl,
Transcribed Image Text:During the synthesis of the antiasthmatic drug montelukast (Singulair), a silyl ether protecting group is used to mask the reactivity of an OH group. The silyl group chosen is the tert-butyldimethylsilyl (TBS) group. Draw the product of the following transforma- tion, assuming the TBS-Cl reagent reacts only once with the starting material. Briefly explain your answer. CH3 НО H3C-C-CH3 H3C-Si-CH3 CH3 H3C OH Cl, CI Imidazole (base) DMF/CH,Cl,
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 5 images

Blurred answer
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY