135149-43-8|tert-Butyl 5-formylthiophene-2-carboxylate| Ambeed

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CAS No. :	135149-43-8
Formula :	C₁₀H₁₂O₃S
M.W :	212.26
SMILES Code :	O=C(C1=CC=C(C=O)S1)OC(C)(C)C
MDL No. :	MFCD25958248

Yield	Reaction Conditions	Operation in experiment
94%	With pyridine; dmap; In dichloromethane; tert-butyl alcohol; at 20℃; for 24h;	To a solution of <strong>[4565-31-5]5-formyl-2-thiophencarboxylic acid</strong> (25 g,0.16 mol) in tert-butyl alcohol (200 mL) and dichioromethane(100 mL) was added di-tert-butyl dicarbonate (41g, 0.l9mol),N,N-dimethylaminopyridine (2.0 g, 0.016 mol), and pyridine (5mL), and the mixture was stirred at room temperature for 24hours. The reaction mixture was concentrated under reduced pressure. The residue was added to ethyl acetate and 0.5N- hydrochloric acid solution, the organic layer was separated, and the aqueous layer was extracted two times with ethyl acetate. The organic layers were combined, washed with 0.5 Nsodium hydroxide solution and brine, and dried over anhydrous magnesium sulfate. The solvent of the filtrate after filtration was evaporated under reduced pressure to give the title compound (32.1 g, 0.15 mol, 94percent).1HNMR(400MHz, CDCl3) delta 9.95(1H, s), 7.75(1H, d, J=4.0 Hz),7.70(1H, d, J=4.0 Hz), 1.59(9H, s).
94%	With pyridine; dmap; In dichloromethane; tert-butyl alcohol; at 20℃; for 24h;	Step 2. Synthesis of <strong>[4565-31-5]5-formyl-2-thiophencarboxylic acid</strong> tert-butyl ester To a solution of <strong>[4565-31-5]5-formyl-2-thiophencarboxylic acid</strong> (25 g, 0.16 mol) in tert-butyl alcohol (200 mL) and dichloromethane (100 mL) was added di-tert-butyl dicarbonate (41 g, 0.19 mol), N,N-dimethylaminopyridine (2.0 g, 0.016 mol), and pyridine (5 mL), and the mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure. The residue was added to ethyl acetate and 0.5N-hydrochloric acid solution, the organic layer was separated, and the aqueous layer was extracted two times with ethyl acetate. The organic layers were combined, washed with 0.5 N sodium hydroxide solution and brine, and dried over anhydrous magnesium sulfate. The solvent of the filtrate after filtration was evaporated under reduced pressure to give the title compound (32.1 g, 0.15 mol, 94percent). 1H-NMR (400 MHz, CDCl3) delta 9.95 (1H, s), 7.75 (1H, d, J=4.0 Hz), 7.70 (1H, d, J=4.0 Hz), 1.59 (9H, s).
68%	With dmap; In tetrahydrofuran; at 20℃; for 24h;	Example 1tert-Butyl 5-formylthiophene-2-carboxylate To a 100-mL round-bottom flask was added <strong>[4565-31-5]5-formyl-2-thiophenecarboxylic acid</strong> (1.85 g, 11.8 mmol), di-tert-butyldicarbonate (5.69 g, 26.06 mmol), and N,N dimethylaminopyridine (0.289 g, 2.37 mmol) and THF (22 mL). The mixture was stirred at rt for 24 h. The solvent was then removed to give a solid residue to which was added EtOAc (50 mL), sat. NaHCO3 solution (10 mL), and water (10 mL). After separation, the aqueous layer was extracted with EtOAc (2.x.50 mL). The combined organic phases were washed with brine (25 mL), dried (MgSO4), and concentrated. Purification via flash chromatography (hexanes to 10percent EtOAc-hexanes) afforded tert-butyl 5-formylthiophene-2-carboxylate (2.51 g, 68percent) as a white solid; 1H NMR (CDCl3, 400 MHz) delta 9.96 (s, 1H), 7.75 (d, J=3.8 Hz, 1H), 7.70 (d, J=4.0 Hz, 1H), 1.59 (s, 9H).

	With dmap; In dichloromethane; tert-butyl alcohol;	<strong>[4565-31-5]5-Formylthiophene-2-carboxylic acid</strong> (5.27 g, 33.7 mmol), di-tert-butyl dicarbonate (8.1 g, 37.1 mmol) and N,N-dimethylaminopyridine (0.41 g, 3.39 mmol) were dissolved in tert-butanol (120 mL) and dichloromethane (40 mL), and the mixture was stirred overnight.The solvent was evaporated under reduced pressure, and 0.5N aqueous hydrochloric acid solution was added to the residue, and the mixture was extracted with ethyl acetate.The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure.The obtained residue was dissolved in tetrahydrofuran (100 mL) and methanol (10 mL), sodium borohydride (1.28 g, 33.7 mmol) was added at 0°C, and the mixture was stirred for 3 hr.The solvent was evaporated under reduced pressure, 0.5N aqueous hydrochloric acid solution was added to the residue, and the mixture was extracted with ethyl acetate.The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure.The obtained residue was dissolved in dichloromethane (100 mL), methanesulfonyl chloride (2.87 mL, 37.1 mmol) and diisopropylethylamine (8.9 mL, 51.1 mmol) were added at 0°C, and the mixture was stirred for 2 days.The solvent was evaporated under reduced pressure, 0.5N aqueous hydrochloric acid solution was added to the residue, and the mixture was extracted with ethyl acetate.The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure.The obtained residue was purified by silica gel column chromatography to give the title compound (7.5 g).1H-NMR(400MHz, DMSO-d6) delta 7.56(1H, d, J=4.0Hz), 7.04(1H, d, J=4.0Hz), 4.75(2H, s), 1.57(9H, s).
	In N,N-dimethyl-formamide; at 20℃;	Example 685A tert-butyl 5-formylthiophene-2-carboxylate (5709) <strong>[4565-31-5]5-Formylthiophene-2-carboxylic acid</strong> (5.3 g, 33.9 mmol) was taken up in tetrahydrofuran (100 ml) and boc-anhydride (16.30 g, 74.7 mmol) was added, followed by N,N-dimethylaminopyridine (0.829 g, 6.79 mmol). The mixture was stirred overnight at room temperature, during which time the reaction became a dark, purplish color. It was diluted with sat sodium bicarbonate and extracted with ether. The organic layers were dried sodium sulfate, concentrated then purified by normal phase chromatography to give the title compound.

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CAS No.: 135149-43-8

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CAS No.: 135149-43-8

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