Fukuyama Group-Group Meeting Cumulative Examination 1.

Fukuyama Group-Group Meeting Cumulative Examination 07/28/2012
1. Write the pKa value in H 2O.
1)
3)
5)
7)
9)
TMS
N H
TMS
RO
O
Me
Me
Me
H
H
O
OR
2)
4)
6)
Name
MeO H 8) Et3N H
O
F 3C O
H
10)
N
Cl 3C H
H
Ph SH
H
O
S
Me
演習で学ぶ有機反応機構pp.254-257 (化学同人)

2.
3.
Me
OHC
4.
5.
6.
O
OTMS
O
O
Me
MeO
N 3
S
C 10H 11N 3OS
N
H
O
Ph
1) NaH, BrH2C DMF, 60 °C
O •
Ph
PPh 3
Et 2O, rt
Me
2) LiAlH 4, AlCl 3
Et 2O, 0 °C
3) m-CPBA, CH 2Cl 2, rt;
KCN (excess), DMF/H 2O
50 °C
Ph
O
toluene
rt to reflux
92% (2 steps)
C 22H 17NOS
MeO
PPh 3
toluene, rt
99%
N Me
O
H
Me
NH2OH·HCl pyridine
NCS
DMF, rt;
MeN
P
Ph
O Me O
H
Me
O
N
Me
Me
O
MeOH, 45 °C
94%
A, NEt3 THF, 0 °C
65%
toluene
110 °C
54%
CN
O
N
Me
Me
O
Me
Me
H
NaNH 2
bromobenzene
THF
45 °C to reflux
O
42%
CH 2SiMe 3
1) Br 2, AlCl 3, 80 °C
81%
2) trisyl azide, n-Bu 4NBr
18-crown-6, KOH
benzene-H 2O, rt
77%
1) 150 °C, sealed tube
84%
2) n-BuLi, THF
–78 to 0 °C;
i-AmONO, 0 °C to rt
42%
O
i-Pr OTIPS
hν (254 nm)
1,2-dichloroethane;
reflux
62%
3) NaOH aq., NH 3 aq.
NaOCl aq., THF
5 °C to rt
4) hν, Et 2O, –73 °C to rt;
filt.; evap.;
silica gel, Et 2O, rt
60% (2 steps)
Ph
HO
Me
CN
演習で学ぶ有機反応機構C047 (化学同人)
O
N
HN NH
V. H. Rawal et al., J. Am. Chem. Soc., 133, 5798 (2011)
Me
Ph
Ph
M, Alajarin et al., J. Org. Chem., 75, 3737 (2010)
Br
O
O
Me
H
H
S
A
OTIPS
R. L. Danheiser et al., J. Am. Chem. Soc., 116, 9471 (1994)
R. E. Ireland et al., J. Org. Chem., 49, 1001 (1984)
O