* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 30, p. 5924 - 5931
3
[ 65719-09-7 ]
[ 56826-61-0 ]
Yield
Reaction Conditions
Operation in experiment
100%
Stage #1: With lithium aluminium tetrahydride In diethyl ether at 55℃; for 1.5 h; Heating / reflux Stage #2: With water In diethyl ether at 0℃; for 1 h;
Example 6 Diethyl α-(4-hydroxy-3-methoxy-5-methylphenyl)-β-(3-(2-methylpyridyl))ethyl phosphonate A solution of methyl 2-methylnicotinate (35.2 g, 234 mmol) in 275 ml dry ether was added dropwise to a vigorously stirred suspension of LiAlH4 (13.3 g, 350 mmol) in 600 ml dry ether. The reaction mixture was heated to reflux with the oil bath of 55° for 1.5 h and was then cooled to 0°. H2O (64 ml) was added dropwise and, 1 h later, the upper layer was decanted off. The remaining suspension was extracted with ether. The combined organic phases were dried with MgSO4 and evaporated to yield 29.9 g (234 mmol, 100percent) of 3-(hydroxymethyl)-2-methylpyridine as an orange oil; GC-analysis indicated a purity of 100percent.
76%
Stage #1: With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; for 4 h; Stage #2: With water; rochelle salt In hexane; dichloromethane at 0℃;
To a solution of methyl 2-methylnicotinate (5.9 g, 39 mmol) in DCM (100 mL) under argon at -78 0C was added diisobutylaluminium hydride (IM in hexane, 97 mL, 97 mmol). The reaction mixture was stirred for 4 hours and then added to a saturated aqueous solution of Rochelle salt (200 mL) at 0 0C. The mixture was stirred until two layers had formed. The phases were separated and the aqueous phase was extracted with DCM (2 x 150 mL). The combined organic phases were dried (MgSO4) and concentrated in vacuo to give (2- methyl-pyridin-3-yl)-methanol (3.64 g, 76percent) as a yellow oil. Analytical LCMS: (System A, RT = 0.44 min), ES+: 123.9 [MH]+.
Reference：
[1] Canadian Journal of Chemistry, 1995, vol. 73, # 4, p. 531 - 538
[2] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 5, p. 1311 - 1317
6
[ 79-37-8 ]
[ 65719-09-7 ]
[ 23616-31-1 ]
Reference：
[1] Patent: US5391554, 1995, A,
7
[ 65719-09-7 ]
[ 23616-31-1 ]
Reference：
[1] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 5, p. 1311 - 1317
8
[ 67-56-1 ]
[ 201230-82-2 ]
[ 38749-79-0 ]
[ 65719-09-7 ]
Yield
Reaction Conditions
Operation in experiment
93.6%
at 80℃; for 16 h;
A mixture of 3-bromo-2-methylpyridine (5.0 g, 29.0 mmol), Pd(dppf)C12 (2.1 g, 2.9 mmol) and Et3N (8.8 g, 87 mmol) in MeOH (250 mL) was stirred at 80 °C and 5OPsi under CO for 1 6h. Solid was then filtered out and the filtrate was concentrated. The residue was purified by column chromatography (PE:EA=5: 1) to give the desired product (4.1 g, 93.6percent). ‘H NMR (CD3OD, 400MHz) (ppm): 8.57 - 8.42 (m, 1H), 8.08 (d, 1=8.0 Hz, 1H),7.10 (dd, 1=4.8, 7.8 Hz, 1H), 3.81 (s, 3H), 2.73 (s, 3H). LCMS (mlz): 152.0 [M+H]+
General procedure: To a solution of carboxylic acid 22 or 29–31 (0.1mol) in dry methanol (150mL), concd H2SO4 (20mL) was added. The mixture was refluxed for 15–20h (LC–MS control). The solvent was removed in vacuo, and the residue was dissolved in H2O. The solution was made alkaline with cold saturated aq K2CO3 and extracted with CH2Cl2 (4×50mL). The combined organic extracts were dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash chromatography (EtOAc as eluent) or distilled in vacuo to give 17–20.
Reference：
[1] Tetrahedron, 2013, vol. 69, # 33, p. 6799 - 6803
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1913 - 1919
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 90℃; for 16 h; Inert atmosphere
A mixture of methyl 2-methylnicotinate (4.1 g, 27.1 mmol), NBS (5.8 g, 32.5 mmol), AIBN (100 mg, 0.61 mmol) in carbon tetrachloride (55 mL) was stirred at 90 °C for 16 h under nitrogen. Once cooled, the reaction mixture was diluted with water (25 mL) and the aqueous layer was extracted with dichloromethane (50 mL x 3). The combined organic layers were concentrated in vacuo, and the resulting residue was purified by flash chromatography on Si02 to give the desired product (5.0 g, 80.6percent). LCMS (mlz): 229.9 (M+ 1).
General procedure: To a solution of carboxylic acid 22 or 29?31 (0.1mol) in dry methanol (150mL), concd H2SO4 (20mL) was added. The mixture was refluxed for 15?20h (LC?MS control). The solvent was removed in vacuo, and the residue was dissolved in H2O. The solution was made alkaline with cold saturated aq K2CO3 and extracted with CH2Cl2 (4×50mL). The combined organic extracts were dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash chromatography (EtOAc as eluent) or distilled in vacuo to give 17?20.
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