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methanol
(E)-β-methoxycarbonylvinyl phenyl sulphone
methyl 3,3-dimethoxypropionate
Conditions | Yield |
---|---|
With sodium for 0.25h; | 100% |
Conditions | Yield |
---|---|
With methanesulfonic acid; Pd(OAc)2 on carbon; Pd(OAc)2 on carbon - molybdovanadophosphate; oxygen at 50℃; under 760.051 Torr; for 8h; Oxidation; Addition; | 95% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; oxygen; copper(l) chloride; dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 50℃; for 5.5h; Product distribution; absence of hexamethylphosphoric triamide, other additives; | 92% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; oxygen; copper(l) chloride; dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 50℃; for 5.5h; | 92% |
Conditions | Yield |
---|---|
With potassium hydride at 10 - 50℃; for 12h; Concentration; Temperature; | 93.5% |
With potassium carbonate at 0 - 30℃; for 12h; Reagent/catalyst; | 81% |
With potassium carbonate at 20℃; for 10.5h; Cooling with ice; |
trimethyl trans-3-methoxyorthoacrylate
trimethyl orthoformate
methyl 3,3-dimethoxypropionate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 100℃; for 2h; | 91% |
3-(Acetyl-isopropyl-amino)-3-methoxy-propionic acid methyl ester
methyl 3,3-dimethoxypropionate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol for 2.5h; Heating; | 90% |
methanol
(E)-1,1,1-trichloro-4-methoxybut-3-en-2-one
methyl 3,3-dimethoxypropionate
Conditions | Yield |
---|---|
With potassium carbonate for 10h; Ambient temperature; | 80% |
methanol
propynoic acid methyl ester
A
methyl 3,3-dimethoxypropionate
B
methyl (Z)-β-methoxyacrylate
Conditions | Yield |
---|---|
With silver trifluoromethanesulfonate at 70℃; for 20h; | A 4% B 78% |
Conditions | Yield |
---|---|
With tributylphosphine In methanol at 20℃; for 168h; | 71% |
methanol
cyclohexa-1,4-diene
A
methyl 3,3-dimethoxypropionate
B
malonaldehydebis(dimethylacetal)
C
malonic acid dimethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride; ozone -40 deg C, then ca. 30 min reflux; Yields of byproduct given; | A 60% B n/a C n/a |
With hydrogenchloride; ozone at -40℃; -40 deg C, then ca. 30 min reflux; Yield given; | A 60% B n/a C n/a |
With hydrogenchloride; ozone at -40℃; Product distribution; | A 60% B n/a C n/a |
methyl crotonate
3-mercapto-2-butanone
A
methyl 3,3-dimethoxypropionate
B
methyl 4,5-dimethylthiophene-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: methyl crotonate; 3-mercapto-2-butanone With sodium methylate In toluene at 15 - 30℃; Industrial scale; Stage #2: With hydrogenchloride In water; toluene Industrial scale; | A n/a B 29.8% |
methyl 3,3-dimethoxypropionate
Conditions | Yield |
---|---|
With methanol In hexane for 72h; Ambient temperature; | 18% |
methanol
levulinic acid methyl ester
A
methyl 3,3-dimethoxypropionate
B
acetic acid methyl ester
C
methyl 3-methoxypropionate
D
malonic acid dimethyl ester
E
Dimethyl succinate
Conditions | Yield |
---|---|
With dihydrogen peroxide; toluene-4-sulfonic acid In water at 80℃; for 6h; Reagent/catalyst; Solvent; Baeyer-Villiger Ketone Oxidation; Overall yield = 22 %; | A 13% B n/a C n/a D 8% E n/a |
methanol
3-oxo-propionic acid ethyl ester
methyl 3,3-dimethoxypropionate
Conditions | Yield |
---|---|
With hydrogenchloride at -5℃; |
sodium methylate
carbonic acid dimethyl ester
acetylene
methyl 3,3-dimethoxypropionate
Conditions | Yield |
---|---|
at 80 - 85℃; |
Conditions | Yield |
---|---|
With potassium methanolate |
methyl 3-methoxyprop-2-enoate
sodium methylate
methyl 3,3-dimethoxypropionate
Conditions | Yield |
---|---|
With N-Phenyl-2-naphthylamine |
methanol
1,1,5,5-tetramethoxy-pent-2-ene
A
methyl 3,3-dimethoxypropionate
B
1,2-dimethoxy 1,2-dimethoxy-ethane
C
Methyl dimethoxyacetate
Conditions | Yield |
---|---|
With hydrogenchloride; ozone 1.) -40 deg C, 2.) reflux, 1 h; Yield given. Multistep reaction; | |
With hydrogenchloride; reflux; ozone |
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
methanol
dimethyl (2E)-pent-2-enedioate
A
Dimethyl oxalate
B
methyl 3,3-dimethoxypropionate
C
Methyl dimethoxyacetate
D
malonic acid dimethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride; ozone 1.) -40 deg C, 2.) reflux, 1 h; Yield given. Multistep reaction; | |
With hydrogenchloride; reflux; ozone |
methanol
dimethyl trans-3-hexene-1,6-dioate
A
methyl 3,3-dimethoxypropionate
B
malonic acid dimethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride; ozone 1.) -40 deg C, 2.) reflux, 1 h; Yield given. Multistep reaction; | |
With hydrogenchloride; reflux; ozone |
methanol
Methyl linoleate
A
methyl 3,3-dimethoxypropionate
B
1,1-dimethoxyhexane
C
Dimethyl azelate
D
9,9-bis(methoxy)nonanoic acid methyl ester
Conditions | Yield |
---|---|
With hydrogenchloride; ozone 1.) 0 deg C, 2.) reflux, ca. 30 min; Yield given. Multistep reaction. Further byproducts given; | |
With hydrogenchloride; ozone 1.) 0 deg C, 2.) reflux, ca. 30 min; Multistep reaction. Further byproducts given; |
methanol
methyl linolenate
A
methyl 3,3-dimethoxypropionate
B
dimethoxypropane
C
Dimethyl azelate
D
9,9-bis(methoxy)nonanoic acid methyl ester
Conditions | Yield |
---|---|
With hydrogenchloride; ozone 1.) 0 deg C, 2.) reflux, ca. 30 min; Yield given. Multistep reaction. Further byproducts given; | |
With hydrogenchloride; ozone 1.) 0 deg C, 2.) reflux, ca. 30 min; Multistep reaction. Further byproducts given; |
methanol
cyclohexa-1,4-diene
A
methyl 3,3-dimethoxypropionate
B
(Z)-3-hexenedioic acid dimethyl ester
C
1,1,3,6,6-Pentamethoxyhexan
D
4,6,6-Trimethoxyhexansaeure-methylester
E
(Z)-1,1,6,6-Tetramethoxy-3-hexen
F
(Z)-6,6-Dimethoxy-3-hexensaeure-methylester
Conditions | Yield |
---|---|
With hydrogenchloride; ozone at -40℃; for 0.583333h; Product distribution; further products were isolated; |
methanol
cyclohexa-1,4-diene
A
methyl 3,3-dimethoxypropionate
B
(Z)-3-hexenedioic acid dimethyl ester
C
1,1,3,6,6-Pentamethoxyhexan
D
(Z)-6,6-Dimethoxy-3-hexensaeure-methylester
Conditions | Yield |
---|---|
With hydrogenchloride; ozone at -40℃; for 0.583333h; |
methanol
cyclohexa-1,4-diene
A
methyl 3,3-dimethoxypropionate
B
(Z)-3-hexenedioic acid dimethyl ester
C
4,6,6-Trimethoxyhexansaeure-methylester
D
(Z)-6,6-Dimethoxy-3-hexensaeure-methylester
Conditions | Yield |
---|---|
With hydrogenchloride; ozone -40 deg C, then 3 d at room temp.; | |
With hydrogenchloride; ozone at -40℃; for 0.583333h; |
methanol
cyclohexa-1,4-diene
A
methyl 3,3-dimethoxypropionate
B
(Z)-3-hexenedioic acid dimethyl ester
C
(Z)-1,1,6,6-Tetramethoxy-3-hexen
D
(Z)-6,6-Dimethoxy-3-hexensaeure-methylester
Conditions | Yield |
---|---|
With hydrogenchloride; ozone Yield given. Multistep reaction; | |
With hydrogenchloride; ozone -40 deg C, then 3 d at room temp.; |
methanol
(Z)-1,1,6,6-Tetramethoxy-3-hexen
A
methyl 3,3-dimethoxypropionate
B
malonaldehydebis(dimethylacetal)
Conditions | Yield |
---|---|
With hydrogenchloride; ozone 1.) -40 deg C, 2.) reflux, 1 h; Yield given. Multistep reaction; | |
With hydrogenchloride; reflux; ozone |
methanol
acrylic acid methyl ester
A
methyl 3,3-dimethoxypropionate
B
methyl (2E)-3-methoxy-2-propenoate
C
methyl 3-methoxypropionate
Conditions | Yield |
---|---|
With supercritical CO2; oxygen; copper dichloride; palladium dichloride at 40℃; for 12h; Product distribution; various catalysts and temperatures; | |
With supercritical CO2; oxygen; copper dichloride; palladium dichloride at 40℃; for 12h; | A 91.7 % Chromat. B 1.2 % Chromat. C 2.0 % Chromat. |
With supercritical CO2; oxygen; dichloro bis(acetonitrile) palladium(II); copper dichloride at 50℃; for 12h; | A 81.1 % Chromat. B 8.8 % Chromat. C 3.5 % Chromat. |
With supercritical CO2; oxygen; copper dichloride; palladium dichloride at 50℃; for 12h; | A 42.9 % Chromat. B 3.1 % Chromat. C 6.6 % Chromat. |
sodium methylate
carbonic acid dimethyl ester
acetylene
A
methyl 3,3-dimethoxypropionate
B
methyl 3-methoxyprop-2-enoate
C
dimethoxysuccinate de methyle
Conditions | Yield |
---|---|
at 80℃; |
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 20℃; for 1.5h; | 100% |
With water; sodium hydroxide at 110℃; for 0.5h; Inert atmosphere; | 95% |
With lithium hydroxide In tetrahydrofuran; methanol; water Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With sodium hydride In 1,2-dimethoxyethane; mineral oil at -5 - 50℃; for 17h; | 100% |
With sodium hydride In 1,2-dimethoxyethane; mineral oil at 20 - 45℃; Inert atmosphere; Cooling with ice; | 83% |
With sodium hydride In 1,2-dimethoxyethane at 0 - 50℃; for 20h; | 73% |
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane; water at 40 - 90℃; for 0.5h; | 100% |
methyl 3,3-dimethoxypropionate
Conditions | Yield |
---|---|
With sodium hexamethyldisilazane In tetrahydrofuran at 0 - 20℃; for 1.5h; Inert atmosphere; | 100% |
methyl 3,3-dimethoxypropionate
3-hydroxy-1,1-dimethoxy-propane
Conditions | Yield |
---|---|
Stage #1: methyl 3,3-dimethoxypropionate With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1h; Stage #2: With water; sodium hydroxide In diethyl ether for 1h; | 99% |
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1h; | 95% |
1,2,3-trimethoxybenzene
methyl 3,3-dimethoxypropionate
(E)-3-(2,4,6-trimethoxy-phenyl)-acrylic acid methyl ester
Conditions | Yield |
---|---|
With hydrogenchloride In water; acetic acid at 25℃; for 1h; Product distribution / selectivity; | 98% |
5-(5-amino-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one
methyl 3,3-dimethoxypropionate
Conditions | Yield |
---|---|
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; Inert atmosphere; | 98% |
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; Inert atmosphere; | 98% |
methyl 3,3-dimethoxypropionate
4-methoxyphenylhydrazine hydrochloride
methyl 5-methoxy-1H-indole-3-carboxylate
Conditions | Yield |
---|---|
With acetic acid at 70℃; for 4.5h; | 97% |
methyl 3,3-dimethoxypropionate
ethylmagnesium bromide
1-(2,2-dimethoxyethyl)cyclopropan-1-ol
Conditions | Yield |
---|---|
titanium(IV) isopropylate In diethyl ether at 25℃; for 18h; Kulinkovich reaction; | 96% |
Stage #1: methyl 3,3-dimethoxypropionate With titanium(IV) isopropylate In tetrahydrofuran; diethyl ether at 0℃; for 0.166667h; Stage #2: ethylmagnesium bromide In tetrahydrofuran; diethyl ether at 10 - 25℃; for 0.5h; | 89% |
With titanium(IV) isopropylate In tetrahydrofuran; diethyl ether at 0 - 20℃; for 8h; Inert atmosphere; |
methyl 3,3-dimethoxypropionate
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane for 4h; Reflux; | 96% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 1.5h; | 94% |
methyl 3,3-dimethoxypropionate
3-(4'-fluorophenyl)-1-(1'-methylethyl)-1H-indole
Conditions | Yield |
---|---|
With water; trichlorophosphate In acetic acid at 25℃; for 9h; Product distribution / selectivity; | 93% |
With water; trichlorophosphate In acetonitrile at 50℃; for 18h; | 53 % Chromat. |
methyl 3,3-dimethoxypropionate
C18H20O4S
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -30℃; for 1h; Inert atmosphere; | 93% |
methyl 3,3-dimethoxypropionate
methyl 3-methoxyprop-2-enoate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 160℃; for 7.5h; | 91% |
methanesulfonic acid at 160℃; for 6h; Product distribution / selectivity; | 85% |
With potassium hydrogensulfate at 150 - 160℃; for 4h; Reagent/catalyst; | 82% |
Conditions | Yield |
---|---|
With sodium hydride In 1,2-dimethoxyethane at 0 - 35℃; for 16.5h; | 90% |
Stage #1: methyl 3,3-dimethoxypropionate With sodium hydride In 1,2-dimethoxyethane; mineral oil at 40 - 50℃; for 0.5h; Stage #2: Methyl formate In 1,2-dimethoxyethane; mineral oil at 0 - 50℃; | 61% |
Stage #1: methyl 3,3-dimethoxypropionate With sodium hydride In 1,2-dimethoxyethane; mineral oil at 40 - 50℃; for 0.5h; Stage #2: Methyl formate In 1,2-dimethoxyethane; mineral oil at 40 - 50℃; for 2h; | 61% |
Conditions | Yield |
---|---|
With sodium hexamethyldisilazane In tetrahydrofuran at 0 - 15℃; for 18h; Inert atmosphere; | 90% |
With sodium hexamethyldisilazane In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 22℃; for 16h; | |
With sodium hexamethyldisilazane In tetrahydrofuran at 0 - 15℃; for 18h; | |
With sodium hexamethyldisilazane In tetrahydrofuran at 0 - 15℃; for 18h; | |
With sodium hexamethyldisilazane In tetrahydrofuran at 0 - 15℃; for 18.1667h; | 100 mg |
methyl 3,3-dimethoxypropionate
1-aminocarbonyl-3-methyl-4-methoxycarbonyl-1,2-diaza-1,3-diene
Conditions | Yield |
---|---|
Stage #1: methyl 3,3-dimethoxypropionate With Dowex 50W In water at 20℃; for 24h; Stage #2: 1-aminocarbonyl-3-methyl-4-methoxycarbonyl-1,2-diaza-1,3-diene With Duolite A 102 In water at 20℃; for 10h; Further stages.; | 89% |
Conditions | Yield |
---|---|
With potassium hydride In tetrahydrofuran at 0 - 25℃; for 5.5h; Reagent/catalyst; | 88.4% |
N-(thiophen-3-yl)acetamide
methyl 3,3-dimethoxypropionate
Conditions | Yield |
---|---|
With hydrogenchloride In dichloromethane for 2h; Ambient temperature; | 88% |
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane at 95℃; for 1h; Inert atmosphere; | 88% |
With hydrogenchloride In 1,4-dioxane at 95℃; for 1h; Inert atmosphere; | 88% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 0 - 25℃; for 5.5h; | 87.8% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 80℃; for 6h; | 87% |
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 40℃; for 3h; | 86% |
Conditions | Yield |
---|---|
With sodium In diethyl ether for 48h; Ambient temperature; | 85% |
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; for 24h; | 85% |
With trifluoroacetic acid In dichloromethane at 20℃; for 8h; Inert atmosphere; |
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