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(3-oxo-2-pentyl-cyclopent-1-enyl)-acetic acid methyl ester
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In cyclohexane at 20℃; under 760 Torr; for 1.5h; | 100% |
methyl 1-carboxymethyl-1-(2-pentyl-3-oxocyclopentyl)acetate
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
With water at 190℃; for 3h; Inert atmosphere; | 97.82% |
With methanol; water at 180℃; for 4h; Inert atmosphere; | 85% |
With water at 215℃; for 4h; |
methyl 1-carboxymethyl-1-(2-pentyl-3-oxocyclopentyl)acetate
A
methanol
B
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
With water at 180 - 215℃; for 3.75 - 15h; Product distribution / selectivity; | A n/a B 93.5% |
methyl 1-carboxymethyl-1-(2-pentyl-3-oxocyclopentyl)acetate
A
methyl 3-oxo-2-pentylcyclopentaneacetate
B
2-(3-oxo-2-pentylcyclopentyl)acetic acid
Conditions | Yield |
---|---|
With water at 180 - 215℃; for 4 - 16h; Product distribution / selectivity; | A 90.7% B n/a |
methyl jasmonate
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
With hydrogen; [(C6Me6)2Ru2(PPh2)H2][BF4] In ethanol at 60℃; under 37503 Torr; for 24h; | 90% |
With 10% Pd/C; hydrogen |
2-pentyl-2-cyclopenten-1-one
malonic acid dimethyl ester
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
Stage #1: 2-pentyl-2-cyclopenten-1-one; malonic acid dimethyl ester With sodium methylate In methanol at 0℃; for 5h; Michael addition; Stage #2: In water at 215℃; for 4h; | 28% |
Stage #1: 2-pentyl-2-cyclopenten-1-one; malonic acid dimethyl ester With sodium methylate In methanol at 0℃; for 5h; Michael Condensation; Stage #2: at 215℃; for 4h; |
diazomethane
2-(3-oxo-2-pentylcyclopentyl)acetic acid
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
Yield given; |
2-(1-hydroxypentyl)cyclopent-2-en-1-one
Trimethyl orthoacetate
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
Stage #1: 2-(1-hydroxypentyl)cyclopent-2-en-1-one; Trimethyl orthoacetate With Trimethylacetic acid at 110℃; for 3h; Claisen rearrangement; Stage #2: With hydrogen; palladium on activated charcoal In cyclohexane at 0℃; under 760 Torr; for 18h; |
1-Bromopentane
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 83 percent 2: 87 percent / PPh3 / Pd(OAc)2 / various solvent(s) / 3 h / Heating 3: 88 percent / NaI / hexamethylphosphoric acid triamide / 100 °C 4: 9-BBN 5: CrO3 View Scheme | |
Multi-step reaction with 4 steps 1: ammonia; sodium / -40 - 20 °C 2: di(rhodium)tetracarbonyl dichloride; 4-methylmorpholine N-oxide / 30 h / 80 °C / 3750.38 - 37503.8 Torr / Glovebox; Autoclave 3: sodium methylate / methanol / 2 h / -5 °C / Inert atmosphere 4: water; methanol / 4 h / 180 °C / Inert atmosphere View Scheme |
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CrO3 View Scheme |
2-Pentyl-3-vinyl-cyclopentanone
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 9-BBN 2: CrO3 View Scheme |
2-Oxo-1-pentyl-5-vinyl-cyclopentanecarboxylic acid methyl ester
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 88 percent / NaI / hexamethylphosphoric acid triamide / 100 °C 2: 9-BBN 3: CrO3 View Scheme |
methyl 2-pentyl-3-oxo-8-phenoxy-6-octenoate
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 87 percent / PPh3 / Pd(OAc)2 / various solvent(s) / 3 h / Heating 2: 88 percent / NaI / hexamethylphosphoric acid triamide / 100 °C 3: 9-BBN 4: CrO3 View Scheme |
methyl (E)-3-oxo-8-phenoxy-6-octenoate
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 83 percent 2: 87 percent / PPh3 / Pd(OAc)2 / various solvent(s) / 3 h / Heating 3: 88 percent / NaI / hexamethylphosphoric acid triamide / 100 °C 4: 9-BBN 5: CrO3 View Scheme |
cyclopentanone
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium hydroxide; water / 6 h / 15 °C / Industry scale 2: hydrogen / 5% Pd(II)/C(eggshell); H3PO4/C / 10 h / 140 °C / 757.58 Torr / Inert atmosphere 3: sodium methylate / methanol / 0 °C / Inert atmosphere 4: water / 4 h / 215 °C View Scheme | |
Multi-step reaction with 5 steps 1: sodium hydroxide / water / 6 h / 15 °C / Large scale 2: titanium(IV) oxide / 6 h / 100 °C / 397.54 Torr 3: hydrogenchloride; 3-Methylpyridine / water; butan-1-ol / 4 h / 130 °C 4: sodium methylate / methanol / 5 h / 0 °C / 757.58 Torr / Inert atmosphere 5: 4 h / 215 °C View Scheme |
pentanal
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium hydroxide; water / 6 h / 15 °C / Industry scale 2: hydrogen / 5% Pd(II)/C(eggshell); H3PO4/C / 10 h / 140 °C / 757.58 Torr / Inert atmosphere 3: sodium methylate / methanol / 0 °C / Inert atmosphere 4: water / 4 h / 215 °C View Scheme | |
Multi-step reaction with 5 steps 1: sodium hydroxide / water / 6 h / 15 °C / Large scale 2: titanium(IV) oxide / 6 h / 100 °C / 397.54 Torr 3: hydrogenchloride; 3-Methylpyridine / water; butan-1-ol / 4 h / 130 °C 4: sodium methylate / methanol / 5 h / 0 °C / 757.58 Torr / Inert atmosphere 5: 4 h / 215 °C View Scheme |
2-(1-hydroxypentyl)-cyclopentanone
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogen / 5% Pd(II)/C(eggshell); H3PO4/C / 10 h / 140 °C / 757.58 Torr / Inert atmosphere 2: sodium methylate / methanol / 0 °C / Inert atmosphere 3: water / 4 h / 215 °C View Scheme | |
Multi-step reaction with 4 steps 1: titanium(IV) oxide / 6 h / 100 °C / 397.54 Torr 2: hydrogenchloride; 3-Methylpyridine / water; butan-1-ol / 4 h / 130 °C 3: sodium methylate / methanol / 5 h / 0 °C / 757.58 Torr / Inert atmosphere 4: 4 h / 215 °C View Scheme |
1-Heptyne
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: di(rhodium)tetracarbonyl dichloride; 4-methylmorpholine N-oxide / 30 h / 80 °C / 3750.38 - 37503.8 Torr / Glovebox; Autoclave 2: sodium methylate / methanol / 2 h / -5 °C / Inert atmosphere 3: water; methanol / 4 h / 180 °C / Inert atmosphere View Scheme |
2-pentylidenecyclopentan-1-one
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride; 3-Methylpyridine / water; butan-1-ol / 4 h / 130 °C 2: sodium methylate / methanol / 5 h / 0 °C / 757.58 Torr / Inert atmosphere 3: 4 h / 215 °C View Scheme |
methyl 3-oxo-2-pentylcyclopentaneacetate
2-(3-oxo-2-pentylcyclopentyl)acetic acid
Conditions | Yield |
---|---|
Stage #1: methyl 3-oxo-2-pentylcyclopentaneacetate With sodium hydroxide In methanol at 20℃; for 24h; Stage #2: With hydrogenchloride In methanol; water pH=~ 1; | 99% |
Isopropenyl acetate
methyl 3-oxo-2-pentylcyclopentaneacetate
methyl 2-(3-acetoxy-2-pentylcyclopent-2-en-1-yl)acetate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 90℃; regioselective reaction; | 98% |
With toluene-4-sulfonic acid at 90℃; | 98% |
methyl 3-oxo-2-pentylcyclopentaneacetate
(3-oxo-2-pentyl-cyclopent-1-enyl)-acetic acid methyl ester
Conditions | Yield |
---|---|
With phosphoric acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 101℃; for 5h; | 71.3% |
With iodic acid In dimethyl sulfoxide at 65℃; for 18h; | 65% |
With bromine In acetic acid | |
With 5percent Pd/Alox at 220℃; under 22.5023 Torr; for 24h; Dean-Stark; Inert atmosphere; |
methyl 3-oxo-2-pentylcyclopentaneacetate
methyl 4,5-didehydro-dihydrojasmonate
Conditions | Yield |
---|---|
With trifluoroacetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 80℃; for 48h; | 32% |
With Pd(DMSO)2(trifluoroacetate)2 at 80℃; for 44h; |
methyl 3-oxo-2-pentylcyclopentaneacetate
diazomethyl-trimethyl-silane
3-methoxycarbonylmethyl-2-pentylcyclohexanone
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at -13 - 0℃; for 2.3h; | 19% |
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; toluene at 20℃; for 48h; |
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; toluene for 18h; Product distribution / selectivity; Heating / reflux; |
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydroxide / methanol / 24 h / 20 °C 1.2: pH ~ 1 2.1: magnesium methanolate / methanol / 20 °C / Heating / reflux View Scheme |
methyl 3-oxo-2-pentylcyclopentaneacetate
ethyl 2-cyanoacetate
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid In toluene for 17h; Knoevenagel Condensation; Reflux; Dean-Stark; |
3-amino-2-oxazolidinone
methyl 3-oxo-2-pentylcyclopentaneacetate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 125℃; for 3h; | 0.52 g |
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