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,

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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,
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