157162-16-8|Methyl 3-Hydroxy-5-trifluoromethylthiophene-2-carboxylate| Ambeed

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Quality Control of [ 157162-16-8 ] Purity: 95% SDS Specification

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Product Details of [ 157162-16-8 ]

CAS No. :	157162-16-8
Formula :	C₇H₅F₃O₃S
M.W :	226.17
SMILES Code :	O=C(C1=C(O)C=C(C(F)(F)F)S1)OC
MDL No. :	MFCD05864364
InChI Key :	FUICUPYQNGFYSP-UHFFFAOYSA-N
Pubchem ID :	2759855

Safety of [ 157162-16-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 157162-16-8 ]

* 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.

Downstream synthetic route of [ 157162-16-8 ]

[ 157162-16-8 ] Synthesis Path-Downstream 1~23

1
[ 2365-48-2 ]
[ 144850-59-9 ]
[ 157162-16-8 ]

References: [1]Synthesis,1997,p. 461 - 464.

2
[ 2365-48-2 ]
3,3-Dibromo-4,4,4-trifluoro-butyric acid ethyl ester [ No CAS ]
[ 157162-16-8 ]

References: [1]Synthesis,1997,p. 461 - 464.

3
[ 26717-84-0 ]
[ 2365-48-2 ]
[ 157162-16-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium hydroxide; In methanol;	EXAMPLE 7 Preparation of Methyl 3-Hydroxy-5-trifluoromethyl-2-thiophenecarboxylate STR21 A solution of ethyl 3-methoxy-4,4,4-trifluoro-2-buteneoate (48.45 g, 0.245 mol) and methyl thioglycolate (25.95 g, 0.245 mole) in methanol is treated dropwise with 300 mL, 1M KOH/methanol over a 45 minute period at 35-42 C. (external cooling is used to control exotherm) and stirred at ambient temperatures until reaction is complete by GC analysis. The resultant reaction mixture is poured onto ice water, acidified with 6N H2 SO4 to pH 2 and extracted with ethyl acetate. The ethyl acetate extracts are combined, washed sequentially with saturated NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo to give a pale yellow liquid residue. The residue is vacuum distilled to give the title product as a clear liquid, 39.06 g (71% yield), bp 42-45 C./0.10 mm Hg, identified by 1 H-NMR, 13 C-NMR and 19 FNMR analyses.

References: [1]Patent: US6121202,2000,A .
[2]Synthesis,2000,p. 1078 - 1080.

4
[ 157162-16-8 ]
3-Hydroxy-5-trifluoromethyl-2-thiophenecarboxylic Acid [ No CAS ]

References: [1]Synthesis,2000,p. 1078 - 1080.

5
[ 157162-16-8 ]
[ 217959-45-0 ]

References: [1]Synthesis,2000,p. 1078 - 1080.

6
[ 157162-16-8 ]
[ 74-88-4 ]
methyl 3-methoxy-5-trifluoromethyl-2-thiophenecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate; In dimethyl sulfoxide;	6. Preparation of Methyl 3-methoxy-5-trifluoromethyl-2-thiophenecarboxylate To a solution of 20 g (88 mmole) of methyl 3-hydroxy-5-trifluoromethyl-2-thiophenecarboxylate in 200 mL of DMSO was added 37 g (260 mmole) of methyl iodide and 25 g (181 mmole) of powdered K2CO3. After 2 hr of stirring, the reaction mixture was poured into water and extracted with ether. The organic phase was separated, washed with water several times, dried over MgSO4, filtered and concentrated to give 20 g of a nearly colorless solid. This solid was further purified by recrystallization from 12:1 hexane:ethyl acetate to give 10.5 g of colorless crystals. The mother liquor was concentrated and purified by column chromatography to give another 8 g (87% yield). mp 78-79 C. 1H NMR (300 MHz, CDCl3): δ 7.2 (s, 1H); 4.0 (s, 3H); 3.9 (s, 3H). Anal. Calc'd for C8H7F3O3S: C, 40.00; H, 2.94; S, 13.35. Found: C, 39.87; H, 2.94; S, 13.47.

References: [1]Patent: US2002/94935,2002,A1 .

Yield	Reaction Conditions	Operation in experiment
65%		5B Methyl (3-hydroxy-5-trifluoromethylthien-2-yl)-carboxylate A solution of 1 M potassium hydroxide in methanol (30 ml) is added to a cooled mixture of 5A (4.6 g), methyl thioglycolate (2.46 g) and methanol (10 ml). The resulting reaction mixture was stirred for 24 hours at room temperature. Then the mixture was poured on ice and acidified with 6N sulfuric acid (pH=2). The mixture is extracted with diethyl ether twice. The combined organic phases were washed with water and dried. The mixture was concentrated and the residue is distilled under reduced pressure to yield the product as a clear liquid (3.4 g, 65 %) with a boiling point of 42-45 C. at 0.10 mm.
65%		1B Methyl (3-hydroxy-5-trifluoromethylthien-2-yl)-carboxylate A solution of 1M potassium hydroxide in methanol (30 ml) is added to a cooled mixture of 1A (4.6 g), methyl thioglycolate (2.46 g) and methanol (10 ml). The resulting reaction mixture was stirred for 24 hours at room temperature. Then the mixture was poured on ice and acidified with 6N sulfuric acid (pH=2). The mixture is extracted with diethyl ether twice. The combined organic phases were washed with water and dried. The mixture was concentrated and the residue is distilled under reduced pressure to yield the product as a clear liquid (3.4 g, 65%) with a boiling point of 42-45 C. at 0.10 mm.
65%		2B Methyl (3-hydroxy-5-trifluoromethylthien-2-yl)-carboxylate A solution of 1M potassium hydroxide in methanol (30 ml) is added to a cooled mixture of 2A (4.6 g), methyl thioglycolate (2.46 g) and methanol (10 ml). The resulting reaction mixture was stirred for 24 hours at room temperature. Then the mixture was poured on ice and acidified with 6N sulfuric acid (pH = 2). The mixture is extracted with diethyl ether twice. The combined organic phases were washed with water and dried. The mixture was concentrated and the residue is distilled under reduced pressure to yield the product as a clear liquid (3.4 g, 65 %) with a boiling point of 42-45 C at 0.10 mm.

65%

5B Methyl (3-hydroxy-5-trifluoromethylthien-2-yl)-carboxylate A solution of 1 M potassium hydroxide in methanol (30 ml) is added to a cooled mixture of 5A (4.6 g), methyl thioglycolate (2.46 g) and methanol (10 ml). The resulting reaction mixture was stirred for 24 hours at room temperature. Then the mixture was poured on ice and acidified with 6N sulfuric acid (pH = 2). The mixture is extracted with diethyl ether twice. The combined organic phases were washed with water and dried. The mixture was concentrated and the residue is distilled under reduced pressure to yield the product as a clear liquid (3.4 g, 65 %) with a boiling point of 42-45 C at 0.10 mm.

8
[ 18162-48-6 ]
[ 157162-16-8 ]
[ 912669-49-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20℃;	To a solution of methyl 3-hydroxy-5-trifluoromethyl-2-thiophenecarboxylate (Karp, G.M., et al, Synthesis (2000), 8:1078-1080) (19.4 g, 85.8 mmol) in N1N- dimethylformamide (50.0 mL) was added imidazole (8.77 g, 129 mmol) followed by terf-butyl dimethylsilyl chloride (19.4 g, 129 mmol) at 0 0C. The reaction mixture was stirred at ambient temperature overnight. More imidazole (7.50 g) and te/f-butyl dimethylsilyl chloride (10.5 g) were added. The reaction mixture was stirred for another 4 h and quenched with water (100 mL). The reaction mixture was extracted with ether (3 x 500 mL). The combined organic layers was washed with water (3 x 500 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography eluting with ethyl acetate/hexanes (1/9) to give the titlew compound (26.5 g, 90%) as a yellow oil: 1H NMR (300 MHz, CDCI3) δ 6.91 (s, 1H), 3.82 (s, 3H), 0.21 (s, 6H), 0.06 (s, 9H); 13C NMR (75 MHz, CDCI3) δ 161.5, 155.5, 133.7, 133.2, 123.6 (q, 1JGF = 14.4 Hz), 119.8, 51.9, 25.4, 18.2, -4.6.

References: [1]Patent: WO2006/110917,2006,A2 .Location in patent: Page/Page column 137.

9
[ 75-03-6 ]
[ 157162-16-8 ]
[ 933472-39-0 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide;	7b) S-Ethoxy-δ-trifluoromethyl-thiophene^-carboxylic acid methyl ester (mp.: 93,6C) was prepared from the known S-hydroxy-δ-trifluoromethyl-thiophene^-carboxylic acid methyl ester (Synthesis 2000, No.8, 1078-1080) by alkylation with ethyliodide in the presence of cesium carbonate in DMF as solvent.

References: [1]Patent: WO2007/39173,2007,A1 .Location in patent: Page/Page column 68.

10
[ 157162-16-8 ]
3-benzyl-6-(trifluoromethyl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione [ No CAS ]