1. Provide the major products of each reaction sequence below. 1. PhBr, Pd(PPh,), Cul, NEt, 2. LIAIH, 3. Dess Martin Periodinane 4. CH,CH,CO,Me, LDA then H,0

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter13: Substitution
Section: Chapter Questions
Problem 59CTQ
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1. Phoa pyridine
1. Provide the major products of each reaction sequence below.
1. PhBr, Pd(PPh,), Cul, NEt,
2. LIAIH,
HO,
3. Dess Martin Periodinane
4. CH,CH,CO,Me, LDA then H,0
1.
2. Pd(PPhala, Na;CO,, PhBr
Ph
3. lz. AGOAC
4. КОН, Н.о
OMe
5. TSOH,
1. Ti(OiPr)4. (+)-DET, IBUOOH
(stop at 50% conversion,
remove reacted product)
Ph
Me
Me
2. NaH then Mel
3. O, then Me,S
OH
4. Me,SICH,MgBr then H,SO.
1. CH;0, NH3, NH,CI
2. CBZCI, Na,CO,
3. NH,OH then H,SO,
1. PhO
CI pyridine
2. Bu, SnH, AIBN, A
3. Cp,TICI, Me,AI
4. H,0
5. NABH, CeCl, MeOH
Transcribed Image Text:1. Phoa pyridine 1. Provide the major products of each reaction sequence below. 1. PhBr, Pd(PPh,), Cul, NEt, 2. LIAIH, HO, 3. Dess Martin Periodinane 4. CH,CH,CO,Me, LDA then H,0 1. 2. Pd(PPhala, Na;CO,, PhBr Ph 3. lz. AGOAC 4. КОН, Н.о OMe 5. TSOH, 1. Ti(OiPr)4. (+)-DET, IBUOOH (stop at 50% conversion, remove reacted product) Ph Me Me 2. NaH then Mel 3. O, then Me,S OH 4. Me,SICH,MgBr then H,SO. 1. CH;0, NH3, NH,CI 2. CBZCI, Na,CO, 3. NH,OH then H,SO, 1. PhO CI pyridine 2. Bu, SnH, AIBN, A 3. Cp,TICI, Me,AI 4. H,0 5. NABH, CeCl, MeOH
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