An Efficient Reagent for Deprotection and Selective Oxidative Hydrolysis 919
3
H), 2.92 (dd, J ¼ 6.6 Hz, 14.0 Hz, 1H), 3.22 (dd, J ¼ 7.6 Hz, 14.0 Hz, 1H),
4
.71 (sext, J ¼ 6.8 Hz, 1H), 5.93 (s, 2H), 6.61 (d, J ¼ 7.8 Hz, 1H), 6.63
þ
(
s, 1H), 6.74 (d, J ¼ 7.8 Hz, 1H); MS (ESI): 210 (M þ H) . Anal. calcd. for
C H NO : C, 57.41; H, 5.30; N, 6.70. Found: C, 57.30; H, 5.39; N, 6.78.
1
0
11
4
2
56 cm
-(2-Nitro-propyl)furan (2i). Liquid; IR (neat): y ¼ 3420, 1537,
2
1
1
7
;
H NMR (CDCl ): d ¼ 1.57 (d, J ¼ 6.7 Hz, 3H), 2.37 (dd,
3
J ¼ 7.2 Hz, 15.2 Hz, 1H), 3.80 (dd, J ¼ 6.7 Hz, 15.2 Hz, 1H), 4.84 (sext,
J ¼ 6.8 Hz, 1H), 6.13 (d, J ¼ 2.53 Hz, 1H), 6.30 (d, J ¼ 2.8 Hz, 1H), 7.33
þ
(
s, 1H); MS (ESI): 156 (M þ H) . Anal. calcd. for C H NO : C, 54.19; H,
7
9
3
5
.85; N, 9.03. Found: C, 54.05; H, 5.92; N, 9.10.
2-Nitro-4-(2-nitro-propyl)phenoxy(acetic
(
acid
methyl
2
ester
1 1
(
(
2j). Liquid; IR (neat): y ¼ 3439, 1743, 1626, 814, 755 cm ; H NMR
CDCl ): d ¼ 1.59 (d, J ¼ 6.7 Hz, 3H), 3.04 (dd, J ¼ 5.8 Hz, 14.4 Hz, 1H),
3
3
.30 (dd, J ¼ 8.3 Hz, 14.4 Hz, 1H), 3.80 (s, 3H), 4.74 (s, 2H), 4.75–4.80
(
m, 1H), 6.94 (d, J ¼ 8.6 Hz, 1H), 7.30 (d, J ¼ 8.6 Hz, 1H), 7.71 (s, 1H);
þ
MS (ESI): 299 (M þ H) . Anal. calcd. for C H N O : C, 48.32; H, 4.73;
1
2 14 2 7
N, 9.39. Found: C, 48.21; H, 4.80; N, 9.46.
-(3,4,5-Trimethoxy-phenyl)propan-2-one (3d). Liquid; IR (neat):
1
21 1
y ¼ 3513, 1710, 1590, 917 cm ; H NMR (CDCl ): d ¼ 2.18 (s, 3H), 3.63
3
þ
(
s, 2H), 3.84 (s, 9H), 6.41 (s, 2H); MS (ESI): 225 (M þ H) : Anal. calcd.
for C H O : C, 64.27; H, 7.19. Found: C, 64.41; H, 7.26.
1
2 16 4
1
-(4-Hydroxy–phenyl)propan-2-one (3e). Liquid; IR (neat):
21 1
y ¼ 3357, 1698, 1513, 757 cm ; H NMR (CDCl ): d ¼ 2.16 (s, 3H), 3.63
3
(
s, 2H), 6.40 (brs, OH), 6.80 (d, J ¼ 8.30 Hz, 2H), 7.02 (d, J ¼ 8.30 Hz,
þ
2
H); MS (ESI): 151 (M þ H) . Anal. calcd. for C H O : C, 71.98; H,
9
10 2
6
.71. Found: C, 71.86; H, 6.77.
-(1H-Indol-3-yl)propan-2-one (3f). Mp 104–1068C. IR (KBr):
1
2
1
1
y ¼ 3327, 1708, 752 cm
;
H NMR (CDCl ): d ¼ 2.15 (s, 3H), 3.8
3
(
s, 2H), 7.07 (s, 1H), 7.10–7.23 (m, 2H), 7.34 (d, J ¼ 7.71 Hz, 1H), 7.52
þ
(
d, J ¼ 7.71 Hz, 1H), 8.2 (brs, NH); MS (ESI): 174 (M þ H) . Anal. calcd.
for C H NO: C, 76.28; H, 6.40; N, 8.09. Found: C, 76.13; H, 6.46; N, 8.15.
1
1 11
1
-(4-Amino-phenyl)propan-2-one (3h). Liquid; IR (neat): y ¼ 3363,
2
1 1
1
4
703, 1624, 1515 cm ; H NMR (CDCl ): d ¼ 2.14 (s, 3H), 3.57 (s, 2H),
3
.17 (brs, NH ), 6.49 (d, J ¼ 8.41 Hz, 2H), 7.14 (d, J ¼ 7.95 Hz, 2H); MS
2
þ
(
ESI): 150 (M þ H) . Anal. calcd. for C H NO: C, 72.46; H, 7.43; N,
9
11
9
.39. Found: C, 72.33; H, 7.50; N, 9.48.
1
-Furan-2-yl-propan-2-one(3i). Liquid; IR (neat): y ¼ 3282, 2923,
21 1
712, 743 cm ; H NMR (CDCl ): d ¼ 1.88 (s, 3H), 3.52 (s, 2H), 6.12
1
3
(
d, J ¼ 2.22 Hz, 1H), 6.20 (d, J ¼ 2.90 Hz, 1H), 7.33 (s, 1H); MS (ESI):
þ
1
25 (M þ H) . Anal. calcd. for C H O : C, 67.73; H, 6.50. Found: C,
7
8 2
6
7.99; H, 6.58.
-(2-Oxo-propyl)-4H-benzo(1,4(oxazine-3-one (3j). Mp 154–1568C;
6
2
1 1
IR (KBr): y ¼ 3197, 1710, 1688, 800 cm ; H NMR (CDCl ): d ¼ 2.18
3
(
s, 3H), 3.64 (s, 2H), 4.61 (s, 2H), 6.67 (s, 1H), 6.79 (d, J ¼ 8.16 Hz, 1H),