benzofuran-2(3H)-one
trimethyl orthoformate
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
With acetic anhydride at 95 - 100℃; Concentration; | 96.5% |
With acetic anhydride at 40 - 90℃; Temperature; | 96.8% |
at 110℃; for 21h; Large scale; | |
With zinc(II) chloride at 110℃; for 4h; |
methanol
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
Stage #1: 3-hydroxymethylenebenzofuran-2(3H)-one potassium salt at 10℃; pH=2 - 3; Stage #2: methanol With hydrogenchloride for 4h; Reflux; | 95.2% |
2-Hydroxyphenylacetic acid
trimethyl orthoformate
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
Stage #1: 2-Hydroxyphenylacetic acid With acetic anhydride at 100℃; for 2h; Inert atmosphere; Large scale; Stage #2: trimethyl orthoformate at 100℃; for 19h; Time; Large scale; | 90% |
In 2-Methylpropionic anhydride at 100℃; for 10h; | 59% |
With 2-Methylpropionic anhydride at 100℃; for 10h; | 59% |
With acetic anhydride at 80 - 100℃; for 6h; |
3-formylbenzofuran-2(3H)-one
dimethyl sulfate
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; Time; | 90% |
2-Hydroxyphenylacetic acid
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
With acetic anhydride; trimethyl orthoformate In water; acetic acid; toluene | |
Multi-step reaction with 2 steps 1: acetic anhydride / 2.5 h / 110 °C / Inert atmosphere; Large scale 2: 21 h / 110 °C / Large scale View Scheme | |
Multi-step reaction with 2 steps 1: acetic acid; phosphorus pentoxide / toluene / 6 h / Reflux 2: zinc(II) chloride / 4 h / 110 °C View Scheme |
2-Methylpropionic anhydride
2-Hydroxyphenylacetic acid
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
With trimethyl orthoformate |
benzofuran-2(3H)-one
2-Hydroxyphenylacetic acid
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
With acetic anhydride; trimethyl orthoformate |
benzofuran-2(3H)-one
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
With acetic anhydride; trimethyl orthoformate In methanol; dichloromethane | |
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide / 2 h / -10 - 0 °C 2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: isopropyl alcohol / 20 °C 2.1: sodium hydroxide / methanol / 5 h / 40 °C 2.2: 3 h / Reflux View Scheme |
3-(α-hydroxy)methylenebenzofuran-2(3H)-one
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
With sulfuric acid In methanol |
methanol
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
Stage #1: 3-diethylaminemethylidene-2-benzofuranone With sodium hydroxide In methanol at 40℃; for 5h; Stage #2: methanol With sulfuric acid for 3h; Reflux; |
dimethyl sulfate
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
Stage #1: 3-diethylaminemethylidene-2-benzofuranone With sodium hydroxide In methanol; water at 40℃; for 5h; Stage #2: dimethyl sulfate With tetrabutylammomium bromide In methanol; water at 30℃; for 5h; |
methanol
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
Stage #1: 3-dimethylaminomethylene-2-(3H)benzofuranone With sodium hydroxide In methanol at 40℃; for 5h; Stage #2: methanol With sulfuric acid for 3h; Reflux; |
dimethyl sulfate
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
Stage #1: 3-dimethylaminomethylene-2-(3H)benzofuranone With sodium hydroxide In methanol; water at 40℃; for 5h; Stage #2: dimethyl sulfate With tetrabutylammomium bromide In methanol; water at 30℃; for 5h; |
2'-chloro-benzeneacetic acid
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide; copper(II) oxide / water / pH 7 / Autoclave 2: water / 12 h / 100 °C / Autoclave View Scheme |
benzofuran-2(3H)-one
acetic anhydride
trimethyl orthoformate
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
In water at 100℃; for 12h; Autoclave; |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
benzofurane-3-carboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 0 - 60℃; Solvent; Reagent/catalyst; Temperature; | 97.5% |
4,6-dichloropyrimidine
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
sodium methylate
3-((α)‐2‐(2‐(6‐chloropyrimidin-4‐yl)oxy)phenyl)methyl-3-methoxyacrylate
Conditions | Yield |
---|---|
In tetrahydrofuran; methanol at 3 - 24℃; for 72h; Temperature; Inert atmosphere; Large scale; | 93% |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
sodium methylate
2-(2-hydroxyphenyl)-3,3-dimethoxypropionic acid methyl ester
Conditions | Yield |
---|---|
In methanol at -10℃; for 1h; Inert atmosphere; | 86% |
In methanol at -5 - 0℃; for 1h; | 86% |
methanol
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
2-(2-hydroxyphenyl)-3,3-dimethoxypropionic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: methanol With sodium at -10℃; for 0.5h; Stage #2: 3-(α-methoxy)methylene benzofuran-2-(3H)-ketone for 1h; Inert atmosphere; | 86% |
With sodium at 0℃; for 1h; |
methanol
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
sodium methylate
2-(2-hydroxyphenyl)-3,3-dimethoxypropionic acid methyl ester
Conditions | Yield |
---|---|
at -5 - 0℃; for 1h; | 86% |
4,6-dichloropyrimidine
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
sodium methylate
2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: 3-(α-methoxy)methylene benzofuran-2-(3H)-ketone; sodium methylate With 2-methyl-1,4-divinylpiperazine In methanol; acetonitrile at 15 - 20℃; for 0.5h; Stage #2: 4,6-dichloropyrimidine In methanol; acetonitrile for 1h; Solvent; Temperature; | 85% |
With 2-methyl-1,4-divinylpiperazine In tetrahydrofuran; methanol at 15 - 20℃; for 5h; Solvent; Temperature; Reagent/catalyst; | 80% |
Stage #1: 3-(α-methoxy)methylene benzofuran-2-(3H)-ketone; sodium methylate With potassium carbonate In methanol; toluene at 0℃; for 0.416667h; Inert atmosphere; Stage #2: 4,6-dichloropyrimidine With 1,4-diaza-bicyclo[2.2.2]octane In methanol; toluene for 1h; Reagent/catalyst; Temperature; Solvent; | 55.2% |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
3-(α-hydroxy)methylenebenzofuran-2(3H)-one
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide In water | |
With hydrogenchloride; sodium hydroxide; sulfuric acid In methanol; water |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
With sodium hydroxide In water | |
With hydrogenchloride; sodium hydroxide; sulfuric acid In methanol; 5,5-dimethyl-1,3-cyclohexadiene; water |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
With potassium hydroxide In water |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
Conditions | Yield |
---|---|
In water |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
methyl 2-(2-(6-chloro-2-methylpyrimidin-4-yloxy)-phenyl)-3,3-dimethoxypropanoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C View Scheme |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
methyl 2-(2-(2,6-dichloropyrimidin-4-yloxy)phenyl)-3,3-dimethoxypropanoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C View Scheme |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
methyl 2-(2-(6-chloro-2-(methylthio)pyrimidin-4-yloxy)phenyl)-3,3-dimethoxypropanoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C View Scheme |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
methyl 2-(2-(6-chloro-2-(o-tolylthio)pyrimidin-4-yloxy)phenyl)-3,3-dimethoxypropanoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C View Scheme |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
methyl 2-(2-(6-chloro-2-(m-tolylthio)pyrimidin-4-yloxy)phenyl)-3,3-dimethoxypropanoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C View Scheme |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
methyl 2-(2-(6-chloro-2-(p-tolylthio)pyrimidin-4-yloxy)phenyl)-3,3-dimethoxypropanoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C View Scheme |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
methyl 2-(2-(6-chloro-2-(pyridin-2-ylthio)pyrimidin-4-yloxy)phenyl)-3,3-dimethoxypropanoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C View Scheme |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
(E)-methyl 2-(2-(6-chloro-2-methylpyrimidin-4-yloxy)phenyl)-3-(methoxy)acrylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C 3: methanesulfonic acid; acetic anhydride / 2 h / 90 °C View Scheme |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
(E)-methyl 2-(2-(2,6-dichloropyrimidin-4-yloxy)phenyl)-3-(methoxy)acrylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C 3: methanesulfonic acid; acetic anhydride / 2 h / 90 °C View Scheme |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
(E)-methyl 2-(2-(6-chloro-2-(methylthio)pyrimidin-4-yloxy)phenyl)-3-(methoxy)acrylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C 3: methanesulfonic acid; acetic anhydride / 2 h / 90 °C View Scheme |
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
(E)-methyl 2-(2-(6-chloro-2-(o-tolylthio)pyrimidin-4-yloxy)phenyl)-3-(methoxy)acrylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: methanol / 1 h / -10 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C 3: methanesulfonic acid; acetic anhydride / 2 h / 90 °C View Scheme |
The systematic name of 3-(Methoxymethylene)-2(3H)-benzofuranone is (3Z)-3-(methoxymethylidene)-1-benzofuran-2(3H)-one. With the CAS registry number 40800-90-6, it is also named as 2(3H)-Benzofuranone,3-(methoxymethylene)-. In addition, its molecular formula is C10H8O3 and molecular weight is 176.17.
The other characteristics of 3-(Methoxymethylene)-2(3H)-benzofuranone can be summarized as: (1)ACD/LogP: 1.80; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 3; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 1; (6)Polar Surface Area: 35.53 Å2; (7)Index of Refraction: 1.665; (8)Molar Refractivity: 48.17 cm3; (9)Molar Volume: 129.6 cm3; (10)Polarizability: 19.09×10-24cm3; (11)Surface Tension: 61 dyne/cm; (12)Density: 1.358 g/cm3; (13)Flash Point: 136.6 °C; (14)Enthalpy of Vaporization: 57.37 kJ/mol; (15)Boiling Point: 331.1 °C at 760 mmHg; (16)Vapour Pressure: 0.000159 mmHg at 25 °C.
People can use the following data to convert to the molecule structure.
(1)SMILES: O=C2Oc1ccccc1/C2=C/OC
(2)InChI: InChI=1/C10H8O3/c1-12-6-8-7-4-2-3-5-9(7)13-10(8)11/h2-6H,1H3/b8-6-
(3)InChIKey: YDHPXCHZYXPZIS-VURMDHGXBS
(4)Std. InChI: InChI=1S/C10H8O3/c1-12-6-8-7-4-2-3-5-9(7)13-10(8)11/h2-6H,1H3/b8-6-
(5)Std. InChIKey: YDHPXCHZYXPZIS-VURMDHGXSA-N
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View