[ CAS No. 41337-81-9 ]

Name: 41337-81-9|Ethyl 6-(hydroxymethyl)picolinate|98%
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COA NMR CNMR HPLC LC-MS

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CAS No. :	41337-81-9	MDL No. :	MFCD09750009
Formula :	C₉H₁₁NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CDFOARSBQKJGNL-UHFFFAOYSA-N
M.W :	181.19 g/mol	Pubchem ID :	10921141
Synonyms :

Safety of [ 41337-81-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 41337-81-9 ]

* 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.

Upstream synthesis route of [ 41337-81-9 ]
Downstream synthetic route of [ 41337-81-9 ]

[ 41337-81-9 ] Synthesis Path-Upstream 1~1

1
[ 41337-81-9 ]
[ 1197-10-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: With sodium hydroxide In methanol; water at 20℃; for 1 h; Stage #2: With hydrogenchloride In methanol; water	6-Hydroxymethyl-pyridine-2-carboxylic acid ethylester (200 mg, 1.1 mmol) (J. Amer. Chem. Soc, 1982, 104,2251-2257) was dissolved in methanol (1 ml). Thereafter, therein 2N NAOH aqueous solution (1 ml) was slowly added dropwise, and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was acidified (pH=3) with 2N HC1. Solvent was concentrated under reduced pressure, then, dissolved in methanol and filtered. The filtrate was concentrated under reduced pressure to give 150 mg (yield: 89percent, white solid) of the target compound. 1H NMR (400MHZ, CD30D) : 55. 05 (s, 2H), 8.34 (d, J=8. OHZ, 1H), 8.47 (d, J=8. OHZ, 1H) 8.73 (d, J=8. OHz, 1H)

Reference： [1] Zeitschrift fuer Naturforschung, B: Chemical Sciences, 1994, vol. 49, # 8, p. 1127 - 1136
[2] Patent: WO2004/113281, 2004, A1, . Location in patent: Page 57
[3] Journal of the American Chemical Society, 1982, vol. 104, # 8, p. 2251 - 2257

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Yield	Reaction Conditions	Operation in experiment
85%	With sodium tetrahydroborate In tetrahydrofuran for 2h; Reflux;
83%	With sodium tetrahydroborate In ethanol at 20℃;
69%	With sodium tetrahydroborate In ethanol at -20℃; for 48h;

62%	With sodium tetrahydroborate In ethanol
61.3%	With sodium tetrahydroborate In ethanol at 80℃; for 16h;
49%	With sodium tetrahydroborate In ethanol Heating;
47%	With sodium tetrahydroborate In ethanol
41%	With sodium tetrahydroborate In ethanol for 2h; Reflux; Inert atmosphere;	A001.1 2,6-Pyridine dicarboxylic acid diethyl eater (27.9 g, 0.125 mol) and NaBH4 (3.8 g, 0.1 mol) were dissolved in dry THF (250 mL) and refluxed for 2 h under moisture protection. The solvent was removed and water (50 mL) was added. After stirring for 10 mm, the mixture was extracted with EA (200 mL*2). The organic phases were combined and dried over Mg504, andthe solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel with PE/EA=1:1 to give the product as colorless solid (28 g in 41% yield). ‘H NMR (DMSO-d6) 8.00 (t, 1H, J=7.6 Hz), 7.91 (d, 1H, J7.2 Hz), 7.71 (d, 1H, J7.6 Hz), 5.56 (t, 1H, J=6.0 Hz), 4.62 (d, 2H, J=6.0 Hz), 4.34 (q, 2H, J=7.2 Hz), 1.33 (d, 3H, J=7.2 Hz).
	With sodium tetrahydroborate In ethanol for 2h; Heating;
	With sodium tetrahydroborate In ethanol at 50℃; for 4h;
	Stage #1: diethyl-2,6-pyridinedicarbonyl ester With sodium tetrahydroborate In ethanol for 19h; Stage #2: With water In dichloromethane	3.1; 3.2 Ethyl 6-(hvdroxymethyl)-2-pyridinecarboxylate; Reaction 12.28g (60mmol) of sodium borohydride were added to a stirred solution of 22.3g (100mmols) of diethyl 2,6-pyridinedicarboxylate in 200ml of ethanol and stirred for 4 hours then a further 570mg (15mmols) of sodium borohydride was added and stirred for 15 hours. Evaporated, dissolved in 200ml of dichloromethane and washed with 50ml water. Aqueous layer extracted three times with dichloromethane and the combined organics washed with brine. Dried, evaporated, triturated with ether and filtered off to give 13.01 g of white solid; Reaction 2; 11.4g (0.3mol) of sodium borohydride was added in one portion to a stirred solution of111.5g (0.5mol) of diethyl 2,6-pyridinedicarboxylate in 1 litre of ethanol and stirred for 6 hours when a further 2.85g (0.075mol) of sodium borohydride were added and the mixture stirred overnight before being evaporated. The residue was dissolved in 800ml dichloromethane and washed with water. The aqueous was extracted with 4x50ml of dichloromethane. The combined organics were dried, evaporated and combined with the product from reaction 1 (13.1g). The combined material was washed through a pad of silica on a large sinter with ethyl acetate (2 litres) which was evaporated and triturated with ether and filtered off to give 72.6g of a white solid. The MLS (mother liquors) were evaporated and biotaged (chromatographed) [ethyl acetate/hexane (3:1)] to give a further 2.9g of product.
	With sodium tetrahydroborate In ethanol at 50℃;
	With sodium tetrahydroborate; ethanol for 2h; Heating / reflux;	13 A solution of diethyl 2,6-pyridine dicarboxylate (25 g, 112 mmol) in ethanol (250 mL) was treated with sodium borohydride (2.33 g, 0.55 equiv) and was refluxed for 2 h. After being cooled to RT, the solution was concentrated to a volume of 50 mL and water (50 mL) was added. The solution was further concentrated to a final volume of about 50 mL and extracted with several 50 mL portions of DCM. The combined DCM extracts were dried with sodium sulfate and concentrated by rotary evaporation to yield compound 13A (18.3 g of). HPLC purity 95%. LC/MS m/z 182 (M+H+).
26.6 g	With sodium tetrahydroborate In ethanol at 20℃;
	With sodium tetrahydroborate In ethanol
	With sodium tetrahydroborate
	With sodium tetrahydroborate; ethanol at 90℃; for 5h; Inert atmosphere;	1.1 Synthesis of ethyl 6-hydroxymethyl-2-carboxylatepyridine 5 g of ethyl 2,6-dicarboxylate pyridine and 0.424 g of sodium borohydride were added to a round-bottomed flask containing 95 mL of absolute ethanol under nitrogen at a flow rate of 1 mL / s, and 2,6-dicarboxylate The molar ratio of pyridine to sodium borohydride was 1: 0.5. The mixture was refluxed at 90 ° C for 5 h, then adjusted to pH 5, extracted with trichloromethane, dried over anhydrous sodium sulfate, evaporated to remove the chloroform and then mixed with methanol and chloroform at a volume ratio of 1:15 Liquid as the mobile phase and silica gel as the stationary phase to obtain ethyl 6-hydroxymethyl-2-formylpyridine.

Yield	Reaction Conditions	Operation in experiment
100%	With thionyl chloride
100%	With thionyl chloride In dichloromethane at 0℃; for 1.5h;	A001.2 Thoroughly dried 6-(hydroxymethyl) pyridine-2-carboxylic acid ethyl ester (28 g, 154 mmol) was dissolved in DCM (400 mL) was added dropwise of 50C12 (56 mL) at 0°C. After 90 mm the solution was allowed to reach room temperature and the excess of 50C12 was removedunder reduced pressure without heating. DCM (500 mL) was added to the oily residue, and the solution was washed with saturated aqueous of NaHCO3 and dried over Na2504. Evaporation of the solvent afforded 2-(chloromethyl)pyridine-6-carboxylic acid ethyl ester (31 g in 100% yield) as an orange oil. ‘H NMR (DMSO-d6) 8.0 1-8.08 (m, 2H), 7.81 (d, 1H, J=7.2 Hz), 4.86 (s, 2H), 4.37 (q, 2H, J=6.0 Hz), 1.34 (t, 3H, J=7.2 Hz).
96%	With thionyl chloride at 0℃; for 1h;

96%	With thionyl chloride at 0℃;
91%	With thionyl chloride; sodium carbonate In water
85.6%	With thionyl chloride at 0 - 20℃; for 18h;
83%	With thionyl chloride at 0℃; for 1.5h;
	With thionyl chloride In chloroform at 20℃; for 1h;
	With thionyl chloride In dichloromethane at 10 - 20℃; for 1.25h;	3 Ethyl 6-(chloromethyl)-2-pyridinecarboxylate; Thionyl chloride (13.8ml) was added over - 15 minutes to a stirred solution of ethyl 6- (hydroxymethyl)-2-pyridinecarboxylate (28.5g) in MDC (200ml) maintaining the temperature at 10-150C using an ice-water bath. On completion of the addition the mixture was stirred at room temperature for 1 hour. The solvent was evaporated and the residue partitioned between toluene (200ml)/saturated bicarb (sodium bicarbonate solution, 200ml). The layers were separated and the organic phase washed with water (150ml). The solvent was evaporated to leave a pale oil which solidified on standing. (31.3g).
29.5 g	With thionyl chloride In dichloromethane at 10 - 25℃; for 1h;
	With thionyl chloride In dichloromethane
	With thionyl chloride In dichloromethane at 20℃; for 5.5h; Cooling with ice;	1.2 synthesis of ethyl 6-chloromethyl-2-pyridinecarboxylate 1.81 g of ethyl 6-hydroxymethyl-2-formate pyridine and 730 yL of thionyl chloride were added to a round bottom flask containing 28 mL of dry methylene chloride, 6-hydroxymethyl-2-formylpyridine and The molar ratio of thionyl chloride was 1: 1, stirred for 30 min on an ice bath, and then stirred at room temperature for 5 h. After the completion of the reaction, the methylene chloride was evaporated to dryness, and the toluene was dissolved. The organic layer was washed with water (0.1 m? / L sodium hydrogencarbonate solution) and then the organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated to remove 6- Chloromethyl-2-carboxylate pyridine.
	Stage #1: ethyl 6-(hydroxymethyl)pyridine-2-carboxylate With thionyl chloride In dichloromethane at 10 - 20℃; for 1.25h; Stage #2: With sodium hydrogencarbonate In water; toluene	1.b Step (b) Ethyl 6-(chloromethyl)-2-pyridinecarboxylate; Thionyl chloride (13.8ml) was added over - 15 minutes to a stirred solution of ethyl 6- (hydroxymethyl)-2-pyridinecarboxylate (28.5g) in MDC (200ml) maintaining the temperature at 10-150C using an ice-water bath. On completion of the addition the mixture was stirred at room temperature for 1 hour. The solvent was evaporated and the residue partitioned between toluene (200ml)/saturated bicarb (sodium bicarbonate solution, 200ml) The layers were separated and the organic phase washed with water (150ml). The solvent was evaporated to leave a pale oil which solidified on standing (31.3g).

[ CAS No. 41337-81-9 ]

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[ 41337-81-9 ] Synthesis Path-Upstream 1~1

[ 41337-81-9 ] Synthesis Path-Downstream 1~52