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Volumn 36, Issue 2, 2007, Pages 326-327

Pyridine-3-carboxylic anhydride (3-PCA): A versatile, practical, and inexpensive reagent for condensation reaction between carboxylic acids and alcohols

(2) Mukaiyama, Teruaki a,b Funasaka, Setsuo a

a KITASATO INSTITUTE (Japan)

b KITASATO UNIVERSITY (Japan)

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[No Author keywords available]

Indexed keywords

EID: 34247282103 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2007.326 Document Type: Article

Times cited : (21)

References (31)

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27
- 34247210273
- 3-PCA was prepared from pyridine-3-carboxylic acid. A solution of pyridine-3-carboxylic acid (1.00 g, 8.12 mmol) and diisopropylethylamine (1.41 mL, 8.12 mol) in THF (18 mL) was stirred for 10 min at 0°C. To the reaction mixture, a solution of triphosgene (402 mg, 1.35 mmol) in THF (2 mL) was added at 0°C, then stirred for 1 h. The reaction mixture was additionally stirred for 1 h at room temperature. After filtration of the reaction mixture to remove diisopropylethylammonium chloride formed, the filtrate was condensed under reduced pressure. After EtOAc was added to the residue, the mixture was washed with water. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate. The solvent was evaporated to afford 898 mg (97, of pyridine-3-carboxylic anhydride as a white solid, mp 121-123°C. IR (neat, cm-1) 1797, 1723. 1H NMR (400 MHz, Acetone-d6) δ 7.66 (ddd, 2H, J, 0.8, 4.8, 8.0 Hz, 8.55 ddd, 2H
- 3: C, 63.16; H, 3.53; N, 12.28%. Found: C, 62.94; H, 3.49; N, 12.21%.

28
- 0000278964
- For the preparation of carboxylic anhydrides using triphosgene, see
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- (1994) J. Org. Chem , vol.59 , pp. 2913
- Kocz, R.¹ Roestamadji, J.² Mobashery, S.³

29
- 34247241710
- Typical experimental procedure for the preparation of 3-phenylpropyl 3-phenylpropanoate is shown in the following: To a stirred solution of 3-phenylpropanoic acid (49.6 mg, 0.33 mmol) in CH2Cl2 (1.5 mL) were successively added pyridine-3-carboxylic anhydride (75.4 mg) and DMAP (0.7 mg) at room temperature. After having been stirred for 10 min, a solution of 3-phenylpropan-1-ol (40.9 mg, 0.30 mmol) in dichloromethane (1.5 mL) was added. After the reaction mixture was stirred for 1 h, it was quenched with saturated aqueous sodium hydrogencarbonate. The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na 2SO4, and evaporated. The crude product was purified by preparative TLC (hexane/EtOAc, 9/1) to afford 3-phenylpropyl 3-phenylpropanoate 77.3 mg, 96, as a colorless oil
- 4, and evaporated. The crude product was purified by preparative TLC (hexane/EtOAc = 9/1) to afford 3-phenylpropyl 3-phenylpropanoate (77.3 mg, 96%) as a colorless oil.

30
- 34247236796
- 4, and evaporated. The crude product was purified by silica-gel column chromatography (hexane/EtOAc = 10/1) to afford α-phenylethyl 2-phenylpropanoate (9.96 g, 96%) as colorless oil.
- 4, and evaporated. The crude product was purified by silica-gel column chromatography (hexane/EtOAc = 10/1) to afford α-phenylethyl 2-phenylpropanoate (9.96 g, 96%) as colorless oil.

31
- 34247189704
- 1HNMR. It indicates that l-phenylethyl pyridine-3-carboxylate is transferred to aqueous layer by acidic workup.
- 1HNMR. It indicates that l-phenylethyl pyridine-3-carboxylate is transferred to aqueous layer by acidic workup.

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