516-09-6|4-Hydroxy-3-methylfuran-2(5H)-one| Ambeed

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Quality Control of [ 516-09-6 ] Purity: 95% SDS Specification

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Product Details of [ 516-09-6 ]

CAS No. :	516-09-6
Formula :	C₅H₆O₃
M.W :	114.10
SMILES Code :	O=C1OCC(O)=C1C
MDL No. :	MFCD01860143
InChI Key :	AFKQLNRCQPXHOF-UHFFFAOYSA-N
Pubchem ID :	54711386

Safety of [ 516-09-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 516-09-6 ]

* 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 [ 516-09-6 ]

[ 516-09-6 ] Synthesis Path-Downstream 1~37

1
[ 609-14-3 ]
[ 516-09-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With bromine; In chloroform; at 0 - 130℃; for 4h;	Example 13: Synthesis of 4-hydroxy-3-methyl-5H-furan-2-one.; [Show Image] A solution of bromine (11.60 g, 71.00 mmol) in chloroform (20 ml) was added dropwise to a solution of ethyl 2-methylacetoacetate (10.00 g, 69.00 mmol) in chloroform (75 ml) at 0C. After addition, stirring was kept for 2 hours at room temperature. The solvent was evaporated to dryness and the residue was heated at 130C for 2 hours. A crude solid was obtained which was purified by silica gel chromatography (CH2Cl2 / MeOH, 12/1) to give 5.50 g (70%) of the aimed productas a white solid. TLC (UV 254 nm): AcOEt / n-hexane / acetic acid, 5 / 10 / 0,5 Rf=0,1. 1H RMN (400 MHz, MeOD): 1.6 (t, 3H, J=1.17 Hz, CH3); 4.6 (q, 2H, J= 1.17 Hz, CH2) allylic coupling (AB system). 13C RMN (100 MHz, MeOD): 5.8 (CH3); 68.3 (CH2); 96.7 (3-C(Me)=); 175.0 (C-OH); 179.1 (C=O).
51%	With bromine; In water; at 0 - 20℃;	To a three neck 100 mL round bottom flask, ethyl 2-methyl-3-oxo-butanoate (20 g, 138.72 mmol) was suspended in water (40 mL) and cooled to 0C. Bromine (7.100 mL, 138.70 mmol) was added to the reaction mixture slowly. The reaction mixture was stirred at room temperature for overnight. After the completion of the reaction, tertiary-butyl methyl ether (100 mL) was added and organic layer was separated which was washed with aqueous sodium thiosulfate (1 M, 50 mL), dried over sodium sulfate, concentrated on rotovap to give colorless liquid (27 g) to which (0.5 mL) was added and the reaction mass was refluxed for overnight. The solid formed was filtered and washed with tertiary-butyl methyl ether (10 mL x 3) to give the desired product (8.0 g, 51 %) as a white solid. H NMR (DMSO-D6, 400MHz): δ 1 1.78 (s, 1 H), δ 4.56 (dd, 2H), δ 1 .57 (t, 3H).

References: [1]Tetrahedron Letters,2011,vol. 52,p. 1202 - 1204.
[2]Patent: EP1939192,2008,A1 .Location in patent: Page/Page column 29.
[3]Patent: WO2015/18434,2015,A1 .Location in patent: Page/Page column 40.
[4]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 2334 - 2338.
[5]Journal of Organic Chemistry,2006,vol. 71,p. 8357 - 8364.
[6]Patent: WO2014/15495,2014,A1 .
[7]Patent: WO2014/150132,2014,A1 .
[8]Patent: WO2015/100147,2015,A1 .
[9]Patent: WO2015/105736,2015,A1 .
[10]Patent: WO2016/127358,2016,A1 .
[11]Helvetica Chimica Acta,2018,vol. 101.

2
[ 117968-50-0 ]
[ 516-09-6 ]
[ 117968-48-6 ]

References: [1]Tetrahedron Letters,1988,vol. 29,p. 1489 - 1492.

3
[ 516-09-6 ]
[ 358-23-6 ]
[ 157123-02-9 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20℃; for 1.5h;	To the solution of 4- hydroxy-3-methylfuran-2(5H)-one (400 mg, 3.51 mmol) in dichloromethane (10 mL) at -78 C was added 2,6-lutidine (0.612 mL, 5.26 mmol) and triflic anhydride (0.711 mL, 4.21 mmol) dropwise. The reaction temperature was maintained at -78 C for 0.5 h before being warmed to rt for lh. The mixture was diluted with DCM (100 mL) and washed with 1 N hydrogen chloride (3 times 100 mL), then with diluted sodium bicarbonate solution, then dried over sodium sulfate, and concentrated to give 4-methyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate. LC/MS: (M+l)+: 247.0 .
	With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20℃; for 1.5h;	To a solution of 4- hydroxy-3-methylfuran-2(5H)-one (400 mg, 3.51 mmol) in dichloromethane (10 mL) at -78 C was added 2,6-lutidine (0.612 mL, 5.26 mmol) and triflic anhydride (0.711 mL, 4.21 mmol) dropwise. The reaction temperature was maintained at -78 C for 0.5 h before being warmed to rt for lh. The mixture was diluted with DCM (100 mL) and washed with IN hydrogen chloride (3 times 100 mL), then with diluted sodium bicarbonate solution, then dried over sodium sulfate, and concentrated to give the title compound. LC/MS: (M+l)+: 247.0. I
	With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20℃; for 1.5h;	Step C: 4-Methyl-5-oxo-2,5-dihvdrofuran-3-yl trifluoromethanesulfonate To a solution of <strong>[516-09-6]4-hydroxy-3-methylfuran-2(5H)-one</strong> (400 mg, 3.51 mmol) in DCM (10 mL) at - 78 C was added 2,6-lutidine (0.612 mL, 5.26 mmol) and trifluoromethanesulfonic anhydride (0.711 mL, 4.21 mmol) dropwise. The reaction mixture was stirred at -78 C for 0.5 h, and at rt for 1 h. The mixture was diluted with DCM (100 mL), washed with 1 N hydrogen chloride (3 x 100 mL) and saturated aqueous sodium bicarbonate, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound. LCMS [M +1]+ = 247.0.

	With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20℃; for 1.5h;	To a solution of 4-hydroxy-3-methylfuran-2(51])-one (400 mg, 3.51 mmol) in DCM (10 mL) at -78 C was added 2,6-lutidine (0.6 12 mL, 5.26 mmol) and trifluoromethanesulfonicanhydride (0.7 11 mL, 4.21 mmol) dropwise. The reaction mixture was stirred at -78 C for 0.5hr, and at rt for 1 hr. The mixture was diluted with DCM (100 mL), washed with 1 N hydrogenchloride (3 x 100 mL) and saturated aqueous sodium bicarbonate, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound. LCMS [M +H] = 247.0.
	With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20℃; for 1.5h;	To a solution of <strong>[516-09-6]4-hydroxy-3-methylfuran-2(5H)-one</strong> (400 mg, 3.51 mmol) in DCM (10 mL) at -78 C was added 2,6-lutidine (0.6 12 mL, 5.26 mmol) and trifluoromethanesulfonic anhydride (0.7 11 mL, 4.21 mmol) dropwise. The reaction mixture was stirred at -78 C for 0.5hr, and at rt for 1 hr. The mixture was diluted with DCM (100 mL), washed with 1 N hydrogen chloride (3 x 100 mL) and saturated aqueous sodium bicarbonate, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound. LCMS [M +H] = 247.0.
	With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20℃; for 1.5h;	INTERMEDIATE 31 4-methyl-5-oxo-2,5-dihvdrofuran-3-yl trifluoromethanesulfonate To a solution of <strong>[516-09-6]4-hydroxy-3-methylfuran-2(5H)-one</strong> (INTERMEDIATE 30; 400 mg, 3.51 mmol) in dichloromethane (10 mL) at -78 C was added 2,6-lutidine (0.612 mL, 5.26 mmol) and triflic anhydride (0.71 1 mL, 4.21 mmol) dropwise. The reaction temperature was maintained at - 78 C for 0.5 h before warmed to rt for lh. The mixture was diluted with DCM (100 mL), washed with 1 N hydrogen chloride (3 times 100 mL), diluted sodium bicarbonate solution, dried over sodium sulfate, and concentrated to give 4-methyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate.
	With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20℃; for 1.5h;	4-methyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate To a solution of <strong>[516-09-6]4-hydroxy-3-methylfuran-2(5H)-one</strong> (INTERMEDIATE 30; 400 mg, 3.51 mmol) in dichloromethane (10 mL) at -78 C was added 2,6-lutidine (0.612 mL, 5.26 mmol) and triflic anhydride (0.71 1 mL, 4.21 mmol) dropwise. The reaction temperature was maintained at - 78 C for 0.5 h before warmed to rt for lh. The mixture was diluted with DCM (100 mL), washed with 1 N hydrogen chloride (3 times 100 mL), diluted sodium bicarbonate solution, dried over sodium sulfate, and concentrated to give 4-methyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate.
	With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20℃; for 1.5h;	Step C: 4-Methyl-S -oxo-2. S -dihydrofuran-3 -yl trifluoromethanesulfonateTo a solution of 4-hydroxy-3 -methylfuran-2(SI])-one (400 mg, 3.51 mmol) in dichloromethane (10 mL) at -78 C were added 2,6-lutidine (0.612 mL, 5.26 mmol) and trifluoromethanesulfonic anhydride (0.7 11 mL, 4.21 mmol) dropwise. The reaction mixture was stirred at -78 C for 0.5 h,and at rt for 1 h. The mixture was diluted with dichloromethane, washed with 1 N hydrogen chloride three times and saturated sodium bicarbonate solution, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound. LCMS [M +1] = 247.0.
	With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20℃; for 1.5h;	To a solution of <strong>[516-09-6]4-hydroxy-3-methylfuran-2(5H)-one</strong> (400 mg, 3.51 mmol) in dichloromethane (10 mL) at -78 C were added 2,6-lutidine (0.612 mL, 5.26 mmol) and trifluoromethanesulfonic anhydride (0.71 1 mL, 4.21 mmol) dropwise. The reaction mixture was stirred at -78 C for 0.5 h, and at rt for 1 h. The mixture was diluted with dichloromethane, washed with 1 N hydrogen chloride three times and saturated sodium bicarbonate solution, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound. LCMS [M +1]+ = 247.0.
	With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20℃; for 1.5h;	4-methyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate: To a solution of 4- hydroxy-3-methylfuran-2(5H)-one (400 mg, 3.51 mmol) in dichloromethane (10 mL) at -78C was added 2,6-lutidine (0.612 mL, 5.26 mmol) and triflic anhydride (0.71 1 mL, 4.21 mmol) dropwise. The reaction temperature was maintained at -78C for 0.5 h before being warmed to rt for lh. The mixture was diluted with DCM (100 mL), washed with 1 N hydrogen chloride (3 times 100 mL) followed by diluted sodium bicarbonate solution, dried over sodium sulfate, and then concentrated to give 4-methyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate. LC/MS: (M+l) : 247.0.
	With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20℃; for 1.5h;	Step C: 4-methyl-S-oxo-2,S-dihydrofuran-3-yl trifluoromethanesulfonate: To the solution of 4- hydroxy-3-methylfuran-2(SI])-one (400 mg, 3.51 mmol) in dichloromethane (10 mL) at -78C was added 2,6-lutidine (0.612 mL, 5.26 mmol) and triflic anhydride (0.711 mL, 4.21 mmol) dropwise. The reaction temperature was maintained at -78C for 0.5 h before being warmed to rt for lh. The mixture was diluted with DCM (100 mL) and washed with 1 N hydrogen chloride (3 times 100 mL), then with diluted sodium bicarbonate solution, then dried over sodium sulfate,and concentrated to give 4-methyl-S -oxo-2 ,5 -dihydrofuran-3 -yl trifluoromethanesulfonate.LC/MS: (M+1): 247.0.
	With 2,6-dimethylpyridine; In dichloromethane; at -78℃; for 1.5h;	To a solution of <strong>[516-09-6]4-hydroxy-3-methylfuran-2(5H)-one</strong> (400 mg, 3.51 mmol) in DCM (10 mL) at -78 C. was added 2,6-lutidine (0.612 mL, 5.26 mmol) and trifluoromethanesulfonic anhydride (0.711 mL, 4.21 mmol) dropwise. The reaction mixture was stirred at -78 C. for 0.5 hr, and at rt for 1 hr. The mixture was diluted with DCM (100 mL), washed with 1 N hydrogen chloride (3×100 mL) and saturated aqueous sodium bicarbonate, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound. LCMS [M+H]+=247.0.

References: [1]Tetrahedron,1994,vol. 50,p. 5489 - 5494.
[2]Tetrahedron Letters,2011,vol. 52,p. 1202 - 1204.
[3]Helvetica Chimica Acta,2018,vol. 101.
[4]Patent: WO2014/15495,2014,A1 .Location in patent: Page/Page column 35; 36.
[5]Patent: WO2014/18764,2014,A1 .Location in patent: Page/Page column 37; 38.
[6]Patent: WO2014/150132,2014,A1 .Location in patent: Page/Page column 43.
[7]Patent: WO2015/103756,2015,A1 .Location in patent: Page/Page column 47.
[8]Patent: WO2015/105736,2015,A1 .Location in patent: Page/Page column 49.
[9]Patent: WO2015/96035,2015,A1 .Location in patent: Page/Page column 60.
[10]Patent: WO2015/100147,2015,A1 .Location in patent: Page/Page column 60-61.
[11]Patent: WO2016/8064,2016,A1 .Location in patent: Page/Page column 38.
[12]Patent: WO2016/10801,2016,A1 .Location in patent: Page/Page column 32.
[13]Patent: WO2016/69428,2016,A1 .Location in patent: Page/Page column 26-27.
[14]Patent: WO2016/127358,2016,A1 .Location in patent: Page/Page column 35; 36.
[15]Patent: US2017/37037,2017,A1 .Location in patent: Paragraph 0193.

4
[ 516-09-6 ]
[ 21040-45-9 ]
(phenyl-3 propene-2yl)-3 pentane dione-2,4 [ No CAS ]
[ 115580-41-1 ]
[ 121740-82-7 ]

References: [1]Tetrahedron,1988,vol. 44,p. 7205 - 7212.

5
[ 516-09-6 ]
rac-3-acetoxycyclohexene [ No CAS ]
[ 115580-41-1 ]

References: [1]Tetrahedron Letters,1988,vol. 29,p. 581 - 584.

6
[ 516-09-6 ]
rac-3-acetoxycyclohexene [ No CAS ]
3-(2-cyclohexen-1-yl)-3-methyl-3H,5H-furan-2,4-dione [ No CAS ]

References: [1]Tetrahedron,1988,vol. 44,p. 7205 - 7212.

7
[ 516-09-6 ]
[ 113304-85-1 ]
[ 140902-59-6 ]

References: [1]Journal of Organic Chemistry,1992,vol. 57,p. 2992 - 2993.

8
[ 516-09-6 ]
[ 35587-72-5 ]

References: [1]Helvetica Chimica Acta,1981,vol. 64,p. 775 - 786.

9
[ 37595-74-7 ]
[ 516-09-6 ]
[ 157123-02-9 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 4325 - 4330.

10
[ 32116-05-5 ]
[ 516-09-6 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 8357 - 8364.

11
[ 516-09-6 ]
[ 78-94-4 ]
[ 856016-89-2 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 8357 - 8364.

12
[ 516-09-6 ]
4-bromo-7a-methyl-7,7a-dihydro-3<i>H</i>,6<i>H</i>-isobenzofuran-1,5-dione [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 8357 - 8364.
[2]Organic Letters,2005,vol. 7,p. 2413 - 2416.

13
[ 516-09-6 ]
[ 856016-89-2 ]

References: [1]Organic Letters,2005,vol. 7,p. 2413 - 2416.

14
[ 516-09-6 ]
3-[(3S,4S)-4-Hydroxy-3-methyl-2-oxo-4-(4-oxo-butyryl)-tetrahydro-furan-3-yl]-propionic acid [ No CAS ]