A. Majee et al. / Tetrahedron Letters 53 (2012) 4433–4435
4435
O
O
O
I
OH
OH
O
NaIO4 (2 equiv.)
+
+
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
NH2OH.HCl (3 equiv.)
DCM
I
0%
O
68%
I
O
NaIO4 (4 equiv.)
+
+
Ph
NH2OH.HCl (6 equiv.)
DCM
I
82%
66%
Scheme 3.
Tetrahedron Lett. 2009, 50, 2668; (h) Rahman, M.; Bagdi, A. K.; Majee, A.; Hajra,
A. Tetrahedron Lett. 2011, 52, 4437.
References and notes
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23. Typical experimental procedure for the synthesis of Piperonal: (entry 4, Table 1) In
a
typical experimental procedure a mixture of benzo[d][1,3]dioxol-5-
ylmethanol (1 mmol, 152 mg), NaIO4 (1 mmol, 213 mg) in 2 ml of DCM was
taken in an open round bottomed flask at room temperature and then
NH2OHÁHCl (1.5 mmol, 105 mg) was added by portion for 5 min. After
completion (TLC), the reaction mixture was diluted with a 1:1 mixture of
water/DCM (10 mL) and washed with 10% (w/v) Na2S2O3 (3 Â 5 ml). Then the
combined organic layer was dried over anhydrous Na2SO4. Evaporation of
solvent furnished the crude product which was subjected to column
chromatography using ethyl acetate-petroleum ether (1:10) to obtain the
analytically pure product as a white solid (122 mg, 80%). mp. 36–38 °C; IR
(KBr) cmÀ1 2966, 1676, 1598, 1481, 1440 cmÀ1 1H NMR (300 MHz, CDCl3) d
;
9.80 (s, 1H), 7.41 (dd, J = 1.5, 1.5 Hz, 1H), 7.33 (d, J = 1.2 Hz, 1H), 6.93 (d,
J = 8.1 Hz, 1H), 6.09 (s, 2H); 13C NMR (75 MHz, CDCl3) d 190.2, 152.9, 148.6,
131.7, 128.5, 108.2, 106.7, 102.0. Tert-butyl 4-formylphenylcarbamate (entry 15,
Table 1): Light yellow liquid. IR (KBr) 3311, 2976, 1714, 1683, 1589 cmÀ1.1H
NMR (300 MHz, CDCl3): d 9.80 (s, 1H), 7.33 (d, J = 4.8 Hz, 2H), 7.25 (d, J = 4.2 Hz,
2H), 6.62 (br, 1H), 1.51 (s, 9H). 4-(Tetrahydro-2H-pyran-2-yloxy)benzaldehyde
(entry 16, Table 1): Colourless liquid. IR (KBr) 2935, 1685, 1595, 1508 cmÀ1 1H
.
NMR (300 MHz, CDCl3): d 9.86 (s, 1H), 7.79 (d, J = 5.1 Hz, 2H), 7.13 (d, J = 5.4 Hz,
2H), 5.52–5.51 (m, 1H), 3.53–3.50 (m, 2H), 1.73–1.67 (m, 2H), 1.61–1.47 (m,
4H).
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