2,6-Pyridinedimethanol

LIGHT YELLOW TO BEIGE CRYSTALLINE POWDER

A solution of compound 6 (9.75 g, 50 mmol) in absolute ethanol (40 ml)and stirred in an ice bath as 7.8 g (4 eq.) of sodium borohydride wasadded in portion over 15 minutes, and the mixture was stirred at 0 for1 hour. The ice bath was removed and stirred at room temperature for 2hours, after which it was heated at reflux on a steam bath for 10 hours.The solvent was distilled in vacuo, the residue was mixed with 40 mL ofacetone, and heated on a steam bath for 1 h, and the solvent was distilledin vacuo. The residue was mixed with 40 mL of aqueous potassiumcarbonate and heated on a steam bath for 1 h, the solvent was distilledin vacuo, and the residue was dissolved in 100 mL of water. The aqueous solution was extracted continuously with CHCl3 for 10h to give 6 g (87percent)of compound 7. 1H NMR (400 MHz, CDCl3) δ 7.70 (t, J = 7.6 Hz, 1H), 7.20 (d, J = 7.7 Hz, 2H), 4.78 (s, 4H).Dimethyl pyridine-2, 6-dicarboxylate (885g, leq) is dissolved in EtOH (4425g, 5 Volume) at room temperature. The NaBH4 (341 g, 2eq) is added slowly to the reaction while keeping the internal temperature below 30°C using an ice bath. The reaction is heated to 35°C forapproximately 2hrs. After reaction completion, the mixture is cooled to room temperature and adjusted with 32percent HC1 solution to pH value of approximately 2.5. The mixture is stirred for 9 using 30percent NaOH solution while maintaining an internal temperature below 30°C and stirred at room temperature for about 30 mm. The solids are removed by filtration. The filtrate is concentrated at 50°C. The concentrated residual is suspended with isopropanol (4160g, 8 vol)/water (416g, 0.8 vol) and heated to 70°C for about lhr. The solution is then cooled to room temperature and stirred for 2hr before cooling to 5-10°C for 30mm. The un-dissolved solids are removed by filtration. The filtrate is concentrated at 50°C. The concentrated residue is charged with dichiommethane (2700g, Svol) and heated to 40 °C for 30mm. The suspension is cooled to 5- 10°C and stirred for 30mins. The solid is collected by filtration and dried under vacuum at 40°C to obtain pyridine-2, 6-diyldimethanol; 540.77g, purity 100percent, yield 85.86percentUnder Ar atmosphere, to dimethyl 2, 6-pyridinedicarboxylate (14) (2.00 g, 10.25 mmol) were added dry THF (51.3 mL, 0.2M solution) and lithium borohydride (1.16 g, 51.3 mmol, 5 eq.), and stirred for 16 hours. Then, in an ice bath, to the mixture was added a few drops of acetic acid to neutralize the mixture, thereby quenching the reaction. The mixture was stirred for a while. Formed crystals were dissolved by adding methanol. Although there was one spot of product as checked by TLC (CHCl2.0 g (10.2 mmol) of the compound prepared in the above step 1) was dissolved in 250 ml of a mixed solvent of methanol: diethyl ether (1: 4, volume ratio), 7.7 g (204.8 mmol) of sodium borohydride was slowly added dropwise, and the mixture was stirred at room temperature for 2 hours. ReactionAfter the completion of the reaction, the mixture was diluted with a saturated aqueous ammonium chloride solution and extracted three times with dichloromethane. Isolated organismThe organic layer was dried over anhydrous sodium sulfate and then filtered under reduced pressure and distilled under reduced pressure. The resulting solid was dried under reduced pressure to give the title compound 0.3G (yield: 21percent)..Sodium borohydride (5 g, 131 mmol) was added portionwise to a solution of dimethyl pyridine-2, 6-dicarboxylate (5.5 g, 28 mmol) in dry EtOH (85 mL) under NA modified procedure by Reichardt was followed.To a solution of diethyl pyridine-2, 6-dicarboxylate (225 mg, 1 mmol) (4) in THF (5 mL) was added portionwise sodium borohydride (370 mg, 10 mmol) at -302.2.2 Asolution of 2, 6-pyridinedicarboxylic acid (3.30 g) in absolute ethyl alcohol (60 mL) was added NaBH

Ligand, used in the synthesis of various metal complexes or catalysts.

Molecular Weight:139.15
XLogP3:-0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:139.063328530
Monoisotopic Mass:139.063328530
Topological Polar Surface Area:53.4
Heavy Atom Count:10
Complexity:87.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes