Page 453 - Advanced Organic Chemistry Part B - Reactions & Synthesis

426 Scheme 5.7. Reduction of Other Functional Groups by
Hydride Donors
CHAPTER 5
Reduction of Halides
Carbon-Carbon Multiple a NaBH
Bonds, Carbonyl 1 (CH ) CHCH 4 CH (CH ) CH
CH 3 2 5 3 3 2 6 3
Groups, and Other DMSO
Functional Groups Cl 67%
2 b NaBH CN
3
3
2 8
2 8
CH 3 (CH ) CH I CH (CH ) CH 3
2
HMPA
88–90%
3 c Br
LiAlH 4
THF, reflux 79%
Sulfonates
4 d CH OSO C H 4 CH 3
2 7 7 LiAlH
2
33%
5 e CH 3 CH OSO CH 3 CH 3 CH 3
2
2
O OH
LiAlH 4
6 f LiCuHC H
4 9
OSO C H
2 7 7
75%
Epoxides
7 g LiAlH 4
O
OH
CH 3 CH 3 89%
Acetylenes
8 h LiAlH 4 CH CH 2 H
3
CH CH C CCH 2 CH 3
3
2
120–125°C, H CH CH 3
2
4.5 h
90%
9 i OCH 3 LiAlH OCH 3
HO 4 HO
CHC CCH 3 CH H
NaOCH ,
3
65°C, 45 min
H CH 3
85%
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