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Synthetic route

acetic acid methyl ester
79-20-9

acetic acid methyl ester

benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -78 - 45℃; for 13h; Inert atmosphere;51%
With potassium tert-butylate 1.) -78 deg C, 2 h, 2.) r.t., 18 h; reflux,1 h;39%
acetic anhydride
108-24-7

acetic anhydride

benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

Conditions
ConditionsYield
Stage #1: benzeneacetic acid methyl ester With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.333333h;
Stage #2: acetic anhydride In tetrahydrofuran at -78 - 0℃;
50%
methanol
67-56-1

methanol

2-diazo-1-phenylbutane-1,3-dione
2009-96-3

2-diazo-1-phenylbutane-1,3-dione

A

methyl 2-benzoylpropionate
32742-19-1, 116782-25-3, 29540-54-3

methyl 2-benzoylpropionate

B

methyl 3-oxo-3-phenylpropionate
614-27-7

methyl 3-oxo-3-phenylpropionate

C

methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

D

2-Methoxy-3-oxo-3-phenylpropionsaeuremethylester
112370-88-4

2-Methoxy-3-oxo-3-phenylpropionsaeuremethylester

Conditions
ConditionsYield
In 1,4-dioxane at 10℃; Product distribution; Mechanism; Irradiation; also thermolysis at 80 deg C, other 2-diazo-1,3-dicarbonyl compounds;A 23.9 % Chromat.
B n/a
C 12.5 % Chromat.
D 27.2 % Chromat.
acetyl chloride
75-36-5

acetyl chloride

benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

Conditions
ConditionsYield
Stage #1: benzeneacetic acid methyl ester With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran; hexane at -78℃; for 0.166667h;
Stage #2: acetyl chloride In tetrahydrofuran; hexane at -78 - 20℃;
1.5 g
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

C18H18O5S

C18H18O5S

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; triethylamine In N,N-dimethyl-formamide at 0 - 25℃; for 2h; stereoselective reaction;94%
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

C18H18O5S

C18H18O5S

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; lithium chloride In acetonitrile at 0 - 25℃; for 2h; stereoselective reaction;93%
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

3-phenyl-4-(piperidin-1-yl)-1H-pyrazol-5-amine

3-phenyl-4-(piperidin-1-yl)-1H-pyrazol-5-amine

5-methyl-2,6-diphenyl-3-(piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one

5-methyl-2,6-diphenyl-3-(piperidin-1-yl)pyrazolo[1,5-a]pyrimidin-7(4H)-one

Conditions
ConditionsYield
With acetic acid for 0.5h; Reflux; Inert atmosphere;88%
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

chlorophosphoric acid diphenyl ester
2524-64-3

chlorophosphoric acid diphenyl ester

(Z)-methyl 2-phenyl-3-(diphenoxyphosphoryloxy)but-2-enoate

(Z)-methyl 2-phenyl-3-(diphenoxyphosphoryloxy)but-2-enoate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; N-ethyl-N,N-diisopropylamine; lithium chloride at 0 - 5℃; for 1h; Inert atmosphere; stereoselective reaction;86%
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

chlorophosphoric acid diphenyl ester
2524-64-3

chlorophosphoric acid diphenyl ester

(E)-methyl 2-phenyl-3-(diphenoxyphosphoryloxy)but-2-enoate

(E)-methyl 2-phenyl-3-(diphenoxyphosphoryloxy)but-2-enoate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 0 - 5℃; for 1h; Inert atmosphere; stereoselective reaction;74%
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

1-Phenyl-2-propyn-1-ol
4187-87-5

1-Phenyl-2-propyn-1-ol

3-oxo-2-phenylbutyric acid 1-phenylprop-2-ynyl ester

3-oxo-2-phenylbutyric acid 1-phenylprop-2-ynyl ester

Conditions
ConditionsYield
In toluene at 20℃; for 122h; Reflux; Inert atmosphere;68%
2-bromo-4-methyl-2H-furan-5-one
59488-94-7

2-bromo-4-methyl-2H-furan-5-one

methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

2-(4-Methyl-5-oxo-2,5-dihydro-furan-2-yl)-3-oxo-2-phenyl-butyric acid methyl ester

2-(4-Methyl-5-oxo-2,5-dihydro-furan-2-yl)-3-oxo-2-phenyl-butyric acid methyl ester

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide for 15h; Ambient temperature;65%
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

thiophenol
108-98-5

thiophenol

methyl 3-oxo-2-phenyl-2-(phenylthio)butanoate

methyl 3-oxo-2-phenyl-2-(phenylthio)butanoate

Conditions
ConditionsYield
With oxygen; potassium iodide; sodium hydroxide In acetonitrile at 80℃; under 760.051 Torr; for 18h; Green chemistry;61%
3-amino-1-phenylpyrazin-2(1H)-one
1425864-74-9

3-amino-1-phenylpyrazin-2(1H)-one

methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

C20H15N3O2
1425865-18-4

C20H15N3O2

Conditions
ConditionsYield
With methanesulfonic acid In acetonitrile at 180℃; for 0.5h; Conrad-Limpach Synthesis; Microwave irradiation;60%
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

3-methyl-4-phenyl-1H-pyrazol-5-ol
64754-67-2

3-methyl-4-phenyl-1H-pyrazol-5-ol

Conditions
ConditionsYield
With ethanol; hydrazine hydrate for 4h; Reflux;55%
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

C18H16O5

C18H16O5

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol; CHF3O3S*C10H24N2 In chloroform at 20℃; Schlenk technique; Inert atmosphere; enantioselective reaction;40%
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

phenylhydrazine
100-63-0

phenylhydrazine

3-methyl-1,4-diphenyl-1H-pyrazol-5-ol

3-methyl-1,4-diphenyl-1H-pyrazol-5-ol

Conditions
ConditionsYield
With ethanol at 70℃; for 4h;23%
2-bromo-4-methyl-2H-furan-5-one
59488-94-7

2-bromo-4-methyl-2H-furan-5-one

methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

A

2-(4-Methyl-5-oxo-2,5-dihydro-furan-2-yl)-3-oxo-2-phenyl-butyric acid methyl ester

2-(4-Methyl-5-oxo-2,5-dihydro-furan-2-yl)-3-oxo-2-phenyl-butyric acid methyl ester

B

(Z)-3-(4-Methyl-5-oxo-2,5-dihydro-furan-2-yloxy)-2-phenyl-but-2-enoic acid methyl ester

(Z)-3-(4-Methyl-5-oxo-2,5-dihydro-furan-2-yloxy)-2-phenyl-but-2-enoic acid methyl ester

Conditions
ConditionsYield
With 18-crown-6 ether; potassium tert-butylate In toluene for 15h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

(E)-3-(4-Methyl-5-oxo-2,5-dihydro-furan-2-yloxy)-2-phenyl-but-2-enoic acid methyl ester

(E)-3-(4-Methyl-5-oxo-2,5-dihydro-furan-2-yloxy)-2-phenyl-but-2-enoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KOBu-t, 18-crown-6 / toluene / 15 h / Ambient temperature
2: benzophenone / acetone / 0.5 h / Irradiation
View Scheme
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

(E)-methyl 2,3-diphenyl-2-butenoate
42443-37-8

(E)-methyl 2,3-diphenyl-2-butenoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-methyl-1H-imidazole; triethylamine / N,N-dimethyl-formamide / 2 h / 0 - 25 °C
2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: 1-methyl-1H-imidazole; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 1 h / 0 - 5 °C / Inert atmosphere
2.1: zinc(II) chloride / tetrahydrofuran; acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere
2.2: 2 h / 0 - 65 °C / Inert atmosphere
View Scheme
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

α carbomethoxy β methyl stilbene cis
42443-38-9

α carbomethoxy β methyl stilbene cis

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N,N,N,-tetramethylethylenediamine; lithium chloride / acetonitrile / 2 h / 0 - 25 °C
2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: lithium chloride; 1-methyl-1H-imidazole; N-ethyl-N,N-diisopropylamine / 1 h / 0 - 5 °C / Inert atmosphere
2.1: zinc(II) chloride / tetrahydrofuran; acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere
2.2: 2 h / 0 - 65 °C / Inert atmosphere
View Scheme
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

C18H18O2

C18H18O2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-methyl-1H-imidazole; triethylamine / N,N-dimethyl-formamide / 2 h / 0 - 25 °C
2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere
View Scheme
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

C18H18O2

C18H18O2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N,N,N,-tetramethylethylenediamine; lithium chloride / acetonitrile / 2 h / 0 - 25 °C
2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere
View Scheme
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

(E)-3-(4-Methoxy-phenyl)-2-phenyl-but-2-enoic acid methyl ester

(E)-3-(4-Methoxy-phenyl)-2-phenyl-but-2-enoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-methyl-1H-imidazole; triethylamine / N,N-dimethyl-formamide / 2 h / 0 - 25 °C
2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere
View Scheme
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

(Z)-3-(4-Methoxy-phenyl)-2-phenyl-but-2-enoic acid methyl ester

(Z)-3-(4-Methoxy-phenyl)-2-phenyl-but-2-enoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N,N,N,-tetramethylethylenediamine; lithium chloride / acetonitrile / 2 h / 0 - 25 °C
2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere
View Scheme
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

A

C17H15ClO2

C17H15ClO2

B

C17H15ClO2

C17H15ClO2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-methyl-1H-imidazole; triethylamine / N,N-dimethyl-formamide / 2 h / 0 - 25 °C
2: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / isopropyl alcohol; water / 4 h / 60 °C / Inert atmosphere
View Scheme
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

A

C17H15ClO2

C17H15ClO2

B

C23H19ClO2

C23H19ClO2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-methyl-1H-imidazole; triethylamine / N,N-dimethyl-formamide / 2 h / 0 - 25 °C
2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere
View Scheme
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

C17H15ClO2

C17H15ClO2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N,N,N,-tetramethylethylenediamine; lithium chloride / acetonitrile / 2 h / 0 - 25 °C
2: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / isopropyl alcohol; water / 1 h / 60 °C / Inert atmosphere
View Scheme
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

C15H14O3

C15H14O3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-methyl-1H-imidazole; triethylamine / N,N-dimethyl-formamide / 2 h / 0 - 25 °C
2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere
View Scheme
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

C15H14O3

C15H14O3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N,N,N,-tetramethylethylenediamine; lithium chloride / acetonitrile / 2 h / 0 - 25 °C
2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere
View Scheme
methyl α-acetylphenylacetate
16648-44-5

methyl α-acetylphenylacetate

C15H14O2S

C15H14O2S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-methyl-1H-imidazole; triethylamine / N,N-dimethyl-formamide / 2 h / 0 - 25 °C
2: N-ethyl-N,N-diisopropylamine; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 2 h / 80 - 85 °C / Inert atmosphere
View Scheme

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