Home Cart Sign in  
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 1255206-68-8 Chemical Structure| 1255206-68-8

Structure of 1255206-68-8

Chemical Structure| 1255206-68-8

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 1255206-68-8 ]

CAS No. :1255206-68-8
Formula : C11H10O3
M.W : 190.20
SMILES Code : O=C1OCC2=C1C=CC(C3OC3)=C2C
MDL No. :MFCD18434504

Safety of [ 1255206-68-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H312-H302-H315-H319-H361-H372-H317-H351-H335-H412
Precautionary Statements:P501-P273-P272-P260-P270-P202-P201-P271-P264-P280-P312-P337+P313-P305+P351+P338-P362+P364-P333+P313-P302+P352+P312-P304+P340+P312-P403+P233-P405
Class:6.1
UN#:2811
Packing Group:

Application In Synthesis of [ 1255206-68-8 ]

* 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 [ 1255206-68-8 ]

[ 1255206-68-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 858671-91-7 ]
  • [ 1255206-68-8 ]
  • [ 1255208-00-4 ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide; at 150℃; for 1h;Microwave irradiation; A mixture of 4-methyl-5 -oxiran-2-yl-2-benzofuran- 1 (3H)-one (700 mg, 3.68 mmol) and 1,1- dimethylethyl 2,5-diazabicyclo[2.2.2]octane-2-carboxylate (748 mgs 3.68 mmol) in 2 mL DMSO was heated under microwave condition (15O0C) for 1 hr. After cooling to rt, the mixture was diluted with water (50 mL), extracted with EtOAc (3 X 50 mL). The combined organic layers were washed with brine and dried over Na2SO45 then concentrated. The residue was purified by TLC (MeOHZDCM=I : 15) to obtain l,l-dimethylethyl5-[2-hydroxy-2-(4-methyl-l-oxo-l,3- dihydro-2-benzofuran-5-yl)ethyl]-2,5-diazabicyclo[2.2.2]octane-2-carboxylate as a mixture of 4 isomers, which was separated by SFC chiral chromatography to obtain four chiral isomers or isomer mixtures A, B, C and D with the same MS m/z 403 (M+l)+.
  • 2
  • [ 1255206-69-9 ]
  • [ 1255206-68-8 ]
YieldReaction ConditionsOperation 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.

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 747 - 752.
[2]Patent: WO2010/129379,2010,A1 .Location in patent: Page/Page column 34.
[3]Patent: WO2013/66714,2013,A1 .Location in patent: Page/Page column 37.
[4]Patent: WO2013/66717,2013,A1 .Location in patent: Page/Page column 23.
[5]Patent: WO2013/62892,2013,A1 .Location in patent: Page/Page column 46; 47.
[6]Patent: WO2013/62900,2013,A1 .Location in patent: Page/Page column 28; 29.
[7]Patent: WO2013/90271,2013,A1 .Location in patent: Page/Page column 30.
[8]Patent: WO2013/39802,2013,A1 .Location in patent: Page/Page column 62.
[9]Patent: WO2013/66718,2013,A2 .Location in patent: Page/Page column 21.
[10]Patent: WO2013/28474,2013,A1 .Location in patent: Page/Page column 28.
[11]Patent: WO2014/15495,2014,A1 .Location in patent: Page/Page column 25; 26.
[12]Patent: WO2014/18764,2014,A1 .Location in patent: Page/Page column 28; 29.
[13]Patent: WO2014/85210,2014,A1 .Location in patent: Page/Page column 24; 25.
[14]Patent: WO2014/99633,2014,A2 .Location in patent: Page/Page column 30; 31.
[15]Patent: WO2014/126944,2014,A2 .Location in patent: Page/Page column 30.
[16]Patent: WO2015/17305,2015,A1 .Location in patent: Page/Page column 41.
[17]Patent: WO2015/65866,2015,A1 .Location in patent: Page/Page column 28.
[18]Patent: WO2015/95097,2015,A2 .Location in patent: Page/Page column 29.
[19]Patent: WO2015/103756,2015,A1 .Location in patent: Page/Page column 44; 45; 46.
[20]Patent: WO2015/105736,2015,A1 .Location in patent: Page/Page column 47; 48.
[21]Patent: WO2015/100147,2015,A1 .Location in patent: Page/Page column 42.
[22]Patent: WO2015/96035,2015,A1 .Location in patent: Page/Page column 41.
[23]Patent: WO2016/65582,2016,A1 .Location in patent: Page/Page column 32-33.
[24]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 697 - 701.
[25]Patent: WO2016/122994,2016,A1 .Location in patent: Page/Page column 34.
[26]Patent: EP2744499,2016,B1 .Location in patent: Paragraph 0080.
[27]Patent: WO2016/127358,2016,A1 .Location in patent: Page/Page column 30.
[28]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5695 - 5702.
[29]Patent: US9493474,2016,B2 .Location in patent: Page/Page column 21.
[30]Patent: WO2016/60941,2016,A1 .Location in patent: Page/Page column 33.
[31]Patent: US2017/37037,2017,A1 .Location in patent: Paragraph 0184.
[32]Patent: EP2755656,2016,B1 .Location in patent: Paragraph 0236; 0238.
 

Historical Records