PYRIDINE, 3-CHLORO-5-(PHENYLMETHOXY)- synthesis
- Product Name:PYRIDINE, 3-CHLORO-5-(PHENYLMETHOXY)-
- CAS Number:251996-81-3
- Molecular formula:C12H10ClNO
- Molecular Weight:219.67
74115-12-1
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Yield: 36%
Reaction Conditions:
with triphenylphosphine;benzyl alcohol in tetrahydrofuran;diethyl ether
Steps:
236.A 5-Chloro-3-benzyloxypyridine
EXAMPLE 236A 5-Chloro-3-benzyloxypyridine To a stirred solution of 5-chloro-3-pyridinol (10 g, 77.19 mmol) in anhydrous tetrahydrofuran (155 mL) at 0° C. and under nitrogen atmosphere was added benzyl alcohol (9.6 mL, 92.63 mmol), triphenylphosphine (26.32 g, 100.35 mmol)) and diethyl azodicarboxylate (15.8 mL, 100.35 mmol). The reaction mixture was stirred at room temperature overnight and the solvent was removed under reduced pressure. The residue (70 g) obtained was treated with diethyl ether (2*300 mL) and the solids were removed by filtration. The filtrate obtained was concentrated under reduced pressure and the residue was purified by silica gel flash chromatography eluding with 5% acetone and hexane to obtain the title compound in 36% (5.8 g) yield. MS (APCI) m/e: 220 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 5.22 (s, 2H), 7.33-7.49 (m, 5H), 7.77 (t, J=5 Hz, 1H), 8.23 (d, J=5 Hz, 1H), 8.34 (d, J=5 Hz, 1H).
References:
Abbott Laboratories US6232320, 2001, B1
74115-12-1
215 suppliers
$9.00/1g
100-39-0
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251996-81-3
16 suppliers
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