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General Procedure:
To a 50-mL round-bottomed flask equipped with an air condenser,
acyl chloride (15 mmol) and potassium hexacyanoferrate(II) (3 mmol)
were added. Then the mixture was heated at 160 ˚C for the
time indicated in Table
[²]
.
After the resulting mixture was cooled to r.t., aldehyde (15 mmol)
and Et3N (1.5 mmol) were added. The mixture was further
stirred for 5-8 min at r.t. The progress of the reaction
was monitored by TLC. After completion of the reaction, CH2Cl2 (20
mL) was added, and the solid was removed by filtration. The filtrate
was then washed with icy H2O (3 × 30 mL), and
dried with anhyd MgSO4. After removal of the solvent
under reduced pressure, the residue was subjected to silica gel
flash column chromatography (PE-EtOAc, 20:1) to obtain
pure product. The analytical data for the representative products
are given below. Cyano(4-methoxyphenyl)methyl
Benzoate (Table 2, entry 8): white solid. IR (KBr): 3057, 2250,
1731, 1610, 1514, 1250, 1060, 702 cm-¹. ¹H
NMR (400 MHz, CDCl3):
δ = 8.05
(d, J = 6.8 Hz, 2 H), 7.56-7.62
(m, 5 H), 7.25 (d,
J = 6.8
Hz, 2 H), 6.65 (s, 1 H), 3.83 (s, 3 H). ¹³C
NMR (100 MHz, CDCl3): δ = 164.6, 161.1,
133.9, 130.1, 129.6, 128.6, 128.2, 123.9, 116.4, 114.6, 63.1, 55.4.
Anal. Calcd for C16H13NO3: C, 71.90;
H, 4.90; N, 5.24. Found: C, 71.96; H, 4.88; N, 5.21.
13
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14 The analytical data for the isolated
representative aroyl cyanide are given below. Benzoyl
Cyanide: white solid. IR (KBr): 3073, 2224, 1679, 1594, 1448,
1255, 974, 697 cm-¹. ¹H
NMR (400 MHz, CDCl3): δ = 8.13-8.15
(m, 2 H), 7.78-7.82 (m, 1 H), 7.59-7.63 (m, 2
H). ¹³C NMR (100 MHz, CDCl3): δ = 167.8,
136.8, 133.2, 130.4, 129.5, 112.6.
For reported cyanohydrin esters,
see:
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