1255206-69-9|4-Methyl-5-vinylisobenzofuran-1(3H)-one| Ambeed

Structure of 1255206-69-9

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Quality Control of [ 1255206-69-9 ] Purity: 97% mix TBC as stabilizer SDS Specification

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Product Details of [ 1255206-69-9 ]

CAS No. :	1255206-69-9
Formula :	C₁₁H₁₀O₂
M.W :	174.20
SMILES Code :	O=C1OCC2=C1C=CC(C=C)=C2C
MDL No. :	MFCD26401764
InChI Key :	PYFRWRLVRDXGPN-UHFFFAOYSA-N
Pubchem ID :	66643922

Safety of [ 1255206-69-9 ]

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 [ 1255206-69-9 ]

* 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.

Downstream synthetic route of [ 1255206-69-9 ]

[ 1255206-69-9 ] Synthesis Path-Downstream 1~35

1
[ 1255206-67-7 ]
potassium vinyltrifluoroborate [ No CAS ]
[ 1255206-69-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In ethanol; at 140℃; for 0.333333h;Microwave irradiation;	5-Bromo-4-memyl-2-benzofuran-l(3H)-one (598 mgs 4.47 mmol), potassium vinyl trifluoroborate (507 mgs 2.23 mmmol), PdCl2(dppf)-CΗ2Cl2Adduct (182 mg, 0.223 rammol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mJL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 0C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 12Og Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4- methyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDCl3): δ ppm 7.76 ( d, J = 8Hz, IH), 7.03(dd, J= 11, 17 Hz5 IH), 5.84 (d, J= 17 Hz5 IH)5 5.55 (d, J- 11 Hz, IH), 5.29 (s5 2H)5 2.34 (s, 3H). LC-MS: M+l= 175; tR = 2.42 min
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation;	5-Bromo-4-methyl-2-benzofuran-l(3H)-one (600 mg, 4.5 mmol), potassium vinyl tnfluoroborate (510 mg, 2.2 mmmol), PdCl2(dppf)-CH2Cl2 Adduct (180 mg, 0.220 mmmol), and TEA (0.62 mL, 4.5 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 minutes. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography (0- 80% ETOAC/Hexane solvent system) to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.76 (d, J= 8Hz, 1H), 7.03(dd, 7= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H). LC-MS: [M+l] = 175.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube;	5-Bromo-4-methyl-2-benzofuran-l(3H)-one (600 mg, 4.5 mmol), potassium vinyl trifluoroborate (510 mg, 2.2 mmmol), PdCl2(dppf)-CH2Cl2 Adduct (180 mg, 0.220 mmmol), and TEA (0.62 mL, 4.5 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, and then heated to 140 C for 20 minutes. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, and dried and evaporated to dryness. The crude product was purified by MPLC chromatography (0- 80% ETOAC Hexane solvent system) to yield 5-ethenyl-4-memyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.76 (d, J= 8Hz, 1H)5 7,03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 1 1 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H). LC-MS: [M+l] = 175.

	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube;	Step C: 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one: 5-Bromo-4-methyl-2-benzofuran-l(3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2C12 Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% EtOAC/Hexane solvent system to yield the title product. LC-MS: M+l= 175 at 2.42 retention time.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube;	Step C: 5-ethenyl-4-methyl-2-benzofuran-U3H -one: 5-Bromo-4-methyl-2-benzofuran-l(3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2C12 Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% EtOAC/Hexane solvent system to yield the title product. LC-MS: M+l= 175 at 2.42 retention time.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Inert atmosphere; Sealed tube; Microwave irradiation;	5-Bromo-4-methyl-2-benzofuran- 1 (3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2C12 Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. LC-MS: M+l= 175.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation;	Step A: 5-Ethenyl-4-methyl-2-benzofuran-l(3H)-one 5- Bromo-4-methyl-2-benzofuran-l(3H)-one (600 mg, 4.5 mmol), potassium vinyl trifluoroborate (510 mg, 2.2 mmmol), PdCl2(dppf)-CH2Cl2 Adduct (180 mg, 0.220 mmmol), and TEA (0.62 mL, 4.5 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography (0-80% ETOAC/Hexane solvent system) to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.76 (d, J= 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H). LC-MS: [M+l] = 175.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; Inert atmosphere; Microwave irradiation;	5-Bromo-4-methyl-2-benzofuran- 1 (3H)-one [INTERMEDIATE 1 ] (600 mg, 4.5 mmol), potassium vinyl trifluoroborate (510 mg, 2.2 mmmol), PdCl2(dppf)-CH2Cl2 Adduct (180 mg, 0.220 mmmol), and TEA (0.62 mL, 4.5 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 minutes. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography (0-80% ETOAC/Hexane solvent system) to yield 5-ethenyl-4-methyl-2- benzofuran- 1 (3H)-one. -NMR (500 MHz, CDC13): δ ppm 7.76 (d, J= 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, = 17 Hz, 1H), 5.55 (d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H). LC-MS: [M+l] = 175.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube;	Step A: 5-ethenyl-4-methyl-2-benzofuran-1 (3H)-one; 5-Bromo-4-methyl-2-benzofuran-1 (3H)one(598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCb(dppf)-CH2CbAdduct (182 mg, 0.223 mmmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 mLethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethylacetate, washed with brine twice, dried and evaporated to dryness. The crude product waspurified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-1(3H)-one. LC-MS: M+1= 175.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube;	5-Bromo-4-methyl-2-benzofuran- 1 (3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2Cl2Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.76 ( d, J = 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); LC-MS: M+l= 175;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation;	5 -Bromo-4-methyl-2-benzofuran- 1 (3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2Cl2Adduct (182 mg, 0.223 mmmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% EtOAc/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDCI3): δ ppm 7.76 ( d, J = 8Hz, 1H), 7.03(dd, J= 1 1 , 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 1 1 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); LC-MS: M+l= 175;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube;	5-Bromo-4-methyl-2-benzofuran-l(3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2C12 Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. -NMR (500 MHz, CDCI3): δ ppm 7.76 ( d, J = 8Hz, 1H), 7.03(dd, J= 1 1, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 1 1 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H). LC-MS: M+l= 175.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube;	Step A: 5-ethenvl-4-methyl-2-benzofuran- 1 (3Th-one: 5-Bromo-4-methyl-2-benzofuran- 1(311)-one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdC12(dppf)-CH2C12 Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mLethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for20 mm. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethylacetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-i(3H)-one. LC-MS: M+1= 175
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube;	5-Bromo-4-methyl-2-benzofuran- 1 (3H)- one (598 mg, 4.47 mmol), potassium yinyl trifluoroborate (507 mg, 2.23 mmmol), Pdcl2(dppf)- cH2cl2Adduct (182 mg, 0.223 mmmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 methanol in a 20 m microwaye tube. The tube was sealed and degassed, then heated to 140 c for20 min. Analysis by Lc-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and eyaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% EtOAc/Hexane solyent system to yield 5-ethenyl-4-methyl-2-benzofuran-1(3H)-one. 1H-NMR (500 MHz,cDcl3): ppm 7.76 (d, J = 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55(d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); Lc-MS: M+1= 175;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube;	Step A: S -ethenyl-4-methyl-2-benzofuran- 1(311)-one: S -Bromo-4-methyl-2-benzofuran- 1(311)-one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdC12(dppf)-CH2Cl2Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 mm. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g RediSep column and 0-80% EtOAC/Hexanesolvent system to yield 5-ethenyl-4-methyl-2-benzofuran-1(3H)-one. ‘H-NMR (500 MHz, CDC13): ö ppm 7.76 (d, J = 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); LC-MS: M+1= 175;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube;	S-Bromo-4-methyl-2-benzofuran-i(311)-one (598 mg, 4.47 mmol), potassium vinyltrifluoroborate (507 mg, 2.23 mmmol), PdC12(dppf)-CH2C12 adduct (182 mg, 0.223 mmmol),and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 mm. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4- methyl-2-benzofuran-1(3H)-one. lH-NMR (500 MHz, CDC13): ö ppm 7.76 (d, J = 8Hz, 1H),7.03(dd, J 11, 17Hz, 1H), 5.84 (d, J 17Hz, 1H), 5.55 (d, J 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s,3H); LC-MS: M+1= 175;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube;	5-Bromo-4-methyl-2-benzofuran-l(3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2Cl2Adduct (182 mg, 0.223 mmmol) and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140C for 20 min. Analysis by LC-LC/MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. ^-NMR (500 MHz, CDCI3): δ ppm 7.76 ( d, J = 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); LC-LC/MS: M+l= 175;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; Inert atmosphere;	5 -Bromo-4-methyl-2-benzofuran- 1 (311)-one (598 mg, 4.47 mmol), potassium vinyltrifluoroborate (507 mg, 2.23 mmol), PdC12(dppf)-CH2Cl2Adduct (182 mg, 0.223 mmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 mm. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120gRedi-sep column and 0-80% ETOAC/Hexane solvent system to yield the title compound. MS [M+H] = 175.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube; Inert atmosphere;	5-Bromo-4-methyl-2-benzofuran-1(3H)-one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmol), PdC12(dppf)-CH2Cl2Adduct (182 mg, 0.223 mmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tubewas sealed and degassed, then heated to 140 C for 20 mm. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield the title compound. MS [M+H]= 175.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; Microwave irradiation; Inert atmosphere;	Step A: 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one: 5-Bromo-4-methyl-2-benzofuran- 1 (3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2C12 adduct (182 mg, 0.223 mmmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% EtOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2- benzofuran- 1 (3H)-one .
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Sealed tube;	Step A: 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one: 5-Bromo-4-methyl-2-benzofuran-l(3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdC dppf)- CH2C12 adduct (182 mg, 0.223 mmmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% EtOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2- benzofuran- 1 (3H)-one.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube;	5-Bromo-4-methyl-2-benzofuran-1 (3H) -one (598 mg, 4.47 mmol) (INTERMEDIATE 1) , potassium vinyl trifluoroborate (507 mg, 2.23 mmmol) , PdCl2 (dppf) -CH2Cl2 adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120gcolumn and 0-80 EtOAc/hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-1 (3H) -one. 1H NMR (500 MHz, CDCl3) : δ ppm 7.76 (d, J 8Hz, 1H) , 7.03 (dd, J 11, 17 Hz, 1H) , 5.84 (d, J 17 Hz, 1H) , 5.55 (d, J 11 Hz, 1H) , 5.29 (s, 2H) , 2.34 (s, 3H) LC-MS: M+1 175.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; Microwave irradiation;	5-Bromo-4-methyl-2-benzofuran- 1 (3H)- one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)- CH2Cl2Adduct (182 mg, 0.223 mmmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDCI3): δ ppm 7.76 ( d, J = 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); LC-MS: M+l= 175;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;	5-bromo-4-methyl-2-benzofuran-1(3H)-one (598 mg, 4.47mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCl2(dppf)-CH2Cl2 Adduct (182 mg, 0.223 mmmol),and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealedand degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixturewas diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product waspurified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system toyield 5-ethenyl-4-methyl-2-benzofuran-1(3H)-one. LC-MS: M+1= 175.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube;	Step A: 5 -ethenyl-4-methyl-2-benzofuran- 1 (311)-one: 5 -Bromo-4-methyl-2-benzofuran- 1(31])-one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdC12(dppf)-CH2Cl2Adduct (182 mg, 0.223 mmmol) , and TEA (0.622 mL, 4.47 mmol) were added to 10 mLethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140C for20 mm. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-1(31])-one. ‘H-NMR (500 MHz,CDC13): ö ppm 7.76 (d, J = 8Hz, 1H), 7.03(dd, J= 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55(d, J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); LC-MS: M+1= 175;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube;	5-Bromo-4-methyl-2-benzofuran- 1 (3H)-one [INTERMEDIATE 11(600 mg, 4.5 mmol), potassium vinyl trifluoroborate (510 mg, 2.2 mmol), PdC12(dppf)-CH2C12 Adduct (180 mg, 0.220 mmol), and TEA (0.62 mE, 4.5 mmol) were added to 10 mE ethanol in a 20 mE microwave tube. The tube was sealed and degassed, then heated to 140 C. for 20 minutes. Analysis by EC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPEC chromatography (0-80% ETOAC/Hexane solvent system) to yield 5-ethenyl-4- methyl-2-benzothran-1 (3H)-one.‘H-NMR (500 MHz, CDC13): ö ppm 7.76 (d, J=8 Hz, 1H),7.03 (dd, J=11, 17 Hz, 1H), 5.84 (d, J=17 Hz, 1H), 5.55 (d,J=11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H). EC-MS: [M+1]=175.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Microwave irradiation; Inert atmosphere;	5-Bromo-4-methyl-2-benzofuran- 1 (3H) one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmmol), PdCi2(dppf)- CH2Cl2Adduct (182 mg, 0.223 mmmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120g RediSep column and 0-80% EtOAc/hexane solvent system to yield 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDCls): δ ppm 7.76 ( d, J = 8Hz, 1H), 7.03(dd, J= 1 1 , 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d, J= 1 1 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H); LC-MS: M+l= 175;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube;	5-Bromo-4-methyl-2-benzofuran-1(3H)-one (598 mg, 4.47 mmol), potassium vinyl trifluoroborate (507 mg, 2.23 mmol), PdCl2(dppf)-CH2Cl2Adduct (182 mg, 0.223 mmol), and TEA (0.622 mL, 4.47 mmol) were added to 10 mL ethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C. for 20 min. Analysis by LC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried and evaporated to dryness. The crude product was purified by MPLC chromatography using a 120 g Redi-sep column and 0-80% ETOAC/Hexane solvent system to yield the title compound. MS [M+H]+=175.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube;	[0237] 5-Bromo-4-methyl-2-benzofuran-1(3H)-one (600 mg, 4.5 mmol), potassium vinyl trifluoroborate (510 mg, 2.2mmmol), PdCl2(dppf)-CH2Cl2 Adduct (180 mg, 0.220 mmmol), and TEA (0.62 mL, 4.5 mmol) were added to 10 mLethanol in a 20 mL microwave tube. The tube was sealed and degassed, then heated to 140 C for 20 min. Analysis byLC-MS showed product peak. The reaction mixture was diluted with ethyl acetate, washed with brine twice, dried andevaporated to dryness. The crude product was purified by MPLC chromatography (0-80% ETOAC/Hexane solventsystem) to yield 5-ethenyl-4-methyl-2-benzofuran-1(3H)-one.1H-NMR (500 MHz, CDCl3): δ ppm 7.76 (d, J = 8Hz, 1H), 7.03(dd, J = 11, 17 Hz, 1H), 5.84 (d, J= 17 Hz, 1H), 5.55 (d,J= 11 Hz, 1H), 5.29 (s, 2H), 2.34 (s, 3H). LC-MS: [M+1] = 175.

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2
[ 1255206-69-9 ]
[ 1255206-68-8 ]

Yield	Reaction Conditions	Operation in experiment
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	5-ethenyI-4-methyl-2-benzofuran-l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 0C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 12Og Redi-sep column eluting with 0- 80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3/i)- one. 1H-NMR (500 MHz5 CDCl3): δ ppm 7.77 ( d5 J= 8 Hz, IH), 7.43 (d, J= 8 Hz, IH), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, IH) , 2.43 (s, 3H). LC-MS: MH-I=I 91; tR = 2.2 min
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	5-ethenyl-4-methyl-2-benzofuran-l(3H)-one (1.5 g, 8.4 mmol) was added to DCM (25 mL) at 0C then meta-chloroperbenzoic acid (2.9 g, 17 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, saturated sodium bicarbonate, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography (eluting with 0-80% EtOAc/hexane solvent system) to yield 4-methyl-5-oxiran-2-yl-2- benzofuran-1 (3H)-one.Ή-NMR (500 MHz, CDC13): δ ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J = 8 Hz, 1H), 5.30 (s, 2 H), 4.12 (s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.74 (dd, J= 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H).LC-MS: [M+l] =191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	5-emenyl-4-memyl-2-benzofuran-l(3H)-one (1.5 g, 8.4 mmol) was added to DCM (25 mL) at 0 C then meia-chloroperbenzoic acid (2.9 g, 17 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, saturated sodium bicarbonate, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography (eluting with 0-80% EtOAc/hexane solvent system) to yield 4-methyl-5- oxiran-2-yl-2-benzofuran- 1 (3H)-one.Ή-NMR (500 MHz, CDC13): 6 ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 (s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.74 (dd, J= 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H).LC-MS: [M+1] =191.

	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	Step D: 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one5-ethenyl-4-methyl-2-benzofuran-l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then m-CPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0- 80% EtOAc/hexane solvent system to yield 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. Ή- NMR (500 MHz, CDC13): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H).
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	Step D: 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one5-ethenyl-4-methyl-2-benzofuran-l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then m-CPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0- 80% EtOAc/hexane solvent system to yield 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H- NMR (500 MHz, CDC13): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H).
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	5 -Ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC through a 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H); LC-MS: M+l=191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	Step B: 4-Methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one (1.5 g, 8.4 mmol) was added to DCM (25 mL) at 0 C then meto-chloroperbenzoic acid (2.9 g, 17 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, saturated sodium bicarbonate, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography (eluting with 0-80% EtOAc/hexane solvent system) to yield 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 (s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.74 (dd, J= 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H).
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	5-ethenyl-4-memyl-2-benzofuran-l(3H)-one (1.5 g, 8.4 mmol) was added to DCM (25 mL) at 0 C then meta-chloroperbenzoic acid (2.9 g, 17 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, saturated sodium bicarbonate, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography (eluting with 0-80% EtOAc/hexane solvent system) to yield 4-methyI-5- oxiran-2-yl-2-benzofuran- 1 (3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 (s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.74 (dd, J= 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). LC-MS: [M+l] =191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃;	4-methyl-5-oxiran-2-yl-2-benzofuran-1 (3H)-one; 5-Ethenyl-4-methyl-2-benzofuran-1(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8mmol) was added and the mixture was stirred at R T overnight. The reaction mixture was washedonce each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLCthrough a 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yieldtarget 4-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one. 1H-NMR (500 MHz, CDCh): ()ppm 7.77( d, J= 8Hz, 1H), 7.43 (d, J= 8Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H),2.735 ( dd, J = 2.2, 5.5 Hz, 1H), 2.43 (s, 3H); LC-MS: M+1=191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	5-ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDCls): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). LC-MS: M+l=191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	5 -ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). LC-MS: M+l=191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	5-ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then m-CPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzomran-l(3H)-one. -NMR (500 MHz, CDCI3): δ ppm 7.77 ( d, J= 8 Hz, IH), 7.43 (d, J= 8 Hz, IH), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, IH) , 2.43 (s, 3H). LC-MS: M+l=191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	Step B: 4-methyl-5-oxiran-2-yl-2-benzofuran- 1 (3Ff)-one: 5-Ethenyl-4-methyl-2-benzofuran-1(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stuffed at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC through a 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yieldtarget 4-methyl-5-oxiran-2-yl-2-benzofuran-1(31])-one. ‘H-NMR (500 MHz, CDC13): ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 (dd, J = 2.2, 5.5 Hz, 1H)
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	<strong>[1255206-69-9]5-ethenyl-4-methyl-2-benzofuran-1(3H)-one</strong> (1.46 g, 8.38 mmol) was added to DCM (25 mL) at O c then mcPBA (2.89 g, 16.8mmol) was added and the mixture was stirred at RT oyernight. The reaction mixture was washedonce each with saturated aqueous Na25203, NaHcO3, and brine. The organie layer was driedoyer Na2504, filtered, and eyaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAclhexane solyent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one. 1H-NMR (500 MHz,CDC13): ppm „7.”7”7 (d, J= 8 Hz, 1H), „7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 (dd, J = 2.2, 5.5 Hz, 1H) „ 2.43 (s, 3H). LC-MS: M+1=191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	Step B: 4-methyl-5-oxiran-2-yl-2-benzofuran- 1 (311)-one: 5-ethenyl-4-methyl-2-benzofuran- 1(311)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g RediSep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-1(311)-one. ‘H-NMR (500 MHz,CDC13): ö ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 (dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). LC-MS: M+1191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	5 -ethenyl-4-methyl-2-benzofuran-1(311)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8mmol) was added and the mixture was stirred at RT overnight. The reaction mixture waswashed once each with saturated aqueous Na2S2O3, NaHCO3, and brine. The organic layer wasdried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield 4-methyl-5-oxiran-2-yl-2-benzofuran-1(311)-one. lH-NMR (500 MHz, CDC13): ö ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 (s, 1 H), 3.27(t, J= 4Hz, 1 H), 2.735 (dd, J = 2.2, 5.5 Hz, 1H)2.43 (s, 3H). LC-MS: M+1191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 16h;	5 -ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT 16 h. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2SC"4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). LC-LC/MS: M+l=191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	<strong>[1255206-69-9]5-ethenyl-4-methyl-2-benzofuran-1(3H)-one</strong> (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C, mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RTovernight. The reaction mixture was washed once each with saturated aqueous Na25203, NaHCO3, and brine. The organic layer was dried over Na2504, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sepcolumn eluting with 0-80% EtOAc/hexane solvent system to yield the title compound. MS[M+H] = 191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	<strong>[1255206-69-9]5-ethenyl-4-methyl-2-benzofuran-1(3H)-one</strong> (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C, mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and evaporated todryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield the title compound. MS[M+H]= 191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃;	Step B: 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one: 5-ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C, then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous a2S203, aHC03, and brine. The organic layer was dried over a2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	Step B: 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one: 5-ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C, then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	5-Ethenyl-4-methyl-2-benzofuran-1 (3H) -one (1.46g, 8.38 mmol) (INTERMEDIATE 30) was added to DCM (25 mL) at 0 then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g REDI-column eluting with 0-80EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-1 (3H) -one. 1H NMR (500 MHz, CDCl3) : δ ppm 7.77 (d, J 8 Hz, 1H) , 7.43 (d, J 8 Hz, 1H) , 5.30 (s, 2 H) , 4.12 (s, 1 H) , 3.27 (t, J 4Hz, 1 H) , 2.735 (dd, J 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H) . LC-MS: M+1 191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	5-ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at rt overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, j= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H), 2.43 (s, 3H). LC-MS: M+l=191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃;	5-Ethenyl-4-methyl-2-benzofuran-1(3H)-one (1.46 g, 8.38mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirredat RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, andbrine. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purifiedby MPLC through a 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one. 1H-NMR (500 MHz, CDCl3): δ ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz,1H), 5.30 (s, 2 H), 4.12 (s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 (dd, J = 2.2, 5.5 Hz, 1H), 2.43 (s, 3H); LC-MS: M+1=191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃;	Step B: 4-methyl-S -oxiran-2-yl-2-benzofuran- 1 (311)-one: 5-ethenyl-4-methyl-2-benzofuran-1(311)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0C then mCPBA (2.89 g, 16.8mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washedonce each with saturated aqueous Na25203, NaHCO3, and brine. The organic layer was driedover Na2504, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-1(31])-one. ‘H-NMR (500 MHz, CDC13): ö ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 (s, 1 H), 3.27 (t,J= 4Hz, 1 H), 2.735 (dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). LC-MS: M+1=191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃;	5-ethenyl-4-methyl-2-benzofuran- 1 (3H)-one (1.5 g, 8.4 mmol) was added to DCM (25 mE) at 0 C. then metachioroperbenzoic acid (2.9 g, 17 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was washed once each with saturated aqueous Na25203, saturated sodium bicarbonate, and brine.The organic layer was dried over Na2504, filtered, and evaporated to dryness. The crude material was purified by MPEC chromatography (eluting with 0-80% EtOAc/hexane solvent system) to yield 4-methyl-5-oxiran-2-yl-2-benzo-furan-1(3H)-one.‘H-NMR (500 MHz, CDC13): ö ppm 7.77 (d, J=8 Hz, 1H), 7.43 (d, J=8 Hz, 1H), 5.30 (s, 2H), 4.12 (s, 1H), 3.27 (t, J=4 Hz, 1H), 2.74 (dd, J=2.2, 5.5 Hz, 1H), 2.43 (s, 3H).EC-MS: [M+1]=191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;Inert atmosphere;	5-ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g RediSep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). LC-MS: M+l=191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	<strong>[1255206-69-9]5-ethenyl-4-methyl-2-benzofuran-1(3H)-one</strong> (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C., mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120 g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield the title compound. MS [M+H]+=191.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	[0238] <strong>[1255206-69-9]5-ethenyl-4-methyl-2-benzofuran-1(3H)-one</strong> (1.5 g, 8.4 mmol) was added to DCM (25 mL) at 0 C then meta-chloroperbenzoic acid (2.9 g, 17 mmol) was added and the mixture was stirred at RT overnight. The reaction mixturewas washed once each with saturated aqueous Na2S2O3, saturated sodium bicarbonate, and brine. The organic layerwas dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography(eluting with 0-80% EtOAc/hexane solvent system) to yield 4-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one. 1H-NMR(500 MHz, CDCl3): δ ppm 7.77 (d, J=8 Hz, 1H), 7.43 (d, J = 8 Hz, 1H), 5.30 (s, 2 H), 4.12 (s, 1H), 3.27 (t, J = 4Hz, 1 H),2.74 (dd, J = 2.2, 5.5 Hz, 1H), 2.43 (s, 3H).LC-MS: [M+1] =191.

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3
[ 1255206-69-9 ]
[ 1433479-68-5 ]

References: [1]Patent: WO2013/66714,2013,A1 .
[2]Patent: WO2013/66714,2013,A1 .

4
[ 1255206-69-9 ]
[ 1433480-75-1 ]

References: [1]Patent: WO2013/66714,2013,A1 .
[2]Patent: WO2013/66714,2013,A1 .

5
[ 1255206-69-9 ]
[ 1433480-93-3 ]

References: [1]Patent: WO2013/66714,2013,A1 .

6
[ 1255206-69-9 ]
[ 1255206-71-3 ]

References: [1]Patent: WO2013/66714,2013,A1 .
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7
[ 1255206-69-9 ]
[ 1433481-40-3 ]

References: [1]Patent: WO2013/66714,2013,A1 .

8
[ 1255206-69-9 ]
4-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-1-{2-[(3R)-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-6-yl]ethyl}piperazin-1-ium trifluoroacetate [ No CAS ]

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9
[ 1255206-69-9 ]
[ 1255206-70-2 ]

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10
[ 1255206-69-9 ]
tert-butyl 9-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-6,9-diazaspiro[4.5]decane-6-carboxylate [ No CAS ]

References: [1]Patent: WO2013/66714,2013,A1 .

11
[ 1255206-69-9 ]
9-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-9-aza-6-azoniaspiro[4.5]decane chloride [ No CAS ]

References: [1]Patent: WO2013/66714,2013,A1 .

12
[ 1255206-69-9 ]
[ 1433485-13-2 ]

References: [1]Patent: WO2013/66714,2013,A1 .

13
[ 1255206-69-9 ]
[ 1433485-07-4 ]

References: [1]Patent: WO2013/66714,2013,A1 .

14
[ 76006-33-2 ]
[ 1255206-69-9 ]

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15
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[ 1255206-69-9 ]

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5-{(1R)-1-hydroxy-2-[(3R)-3-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]amino}pyrrolidin-1-yl]ethyl}-4-methyl-2-benzofuran-1(3H)-one [ No CAS ]

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4-[(2R)-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-1-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-2-one [ No CAS ]