Following is a synthesis for albuterol (Proventil),

Chapter 21, Problem 21.62

(choose chapter or problem)

Following is a synthesis for albuterol (Proventil), currently one of the most widely used inhalation bronchodilators. HO CHO CH2O NaOH 4-Hydroxybenzaldehyde HO CHO HO A O CHO O B O O C D Albuterol CH39S9CH3 CH3 I DMSO, NaH 1 O O O OH NH HO HO OH NH 5498X_21_ch21_p853- 905.indd 903 12/14/10 4:47:27 PM Copyright 2010 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it. 904 Chapter 21 Benzene and the Concept of Aromaticity (a) Propose a mechanism for conversion of 4-hydroxybenzaldehyde to A. (b) Propose reagents and experimental conditions for conversion of A to B. (c) Propose a mechanism for the conversion of B to C. Hint: Think of trimethylsulfonium iodide as producing a sulfur equivalent of a Wittig reagent. (d) Propose reagents and experimental conditions for the conversion of C to D. (e) Propose reagents and experimental conditions for the conversion of D to albuterol. (f) Is albuterol chiral? If so, which of the possible stereoisomers are formed in this synthesis?