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CAS No. : | 95517-07-0 | MDL No. : | MFCD06658289 |
Formula : | C12H14O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 190.24 g/mol | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.42 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 56.09 |
TPSA : | 37.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.2 cm/s |
Log Po/w (iLOGP) : | 2.23 |
Log Po/w (XLOGP3) : | 3.18 |
Log Po/w (WLOGP) : | 2.47 |
Log Po/w (MLOGP) : | 1.92 |
Log Po/w (SILICOS-IT) : | 3.17 |
Consensus Log Po/w : | 2.59 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.27 |
Solubility : | 0.101 mg/ml ; 0.000532 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.63 |
Solubility : | 0.0441 mg/ml ; 0.000232 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.27 |
Solubility : | 0.102 mg/ml ; 0.000538 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.86 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With aluminium trichloride In 1,2-dichloro-benzene at 80℃; for 12h; | |
With aluminium trichloride at 120℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: 5,6,7,8-Tetrahydronaphthalen-1-ol With titanium tetrachloride at 20℃; Stage #2: acetyl chloride at 20 - 120℃; for 1.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at 20℃; for 24h; | |
100% | With potassium carbonate In acetonitrile at 76℃; for 74h; | 1.1a la) Synthesis of l-(5-benzyloxytetralin-6-yl)ethanone ( 1 ) 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (300 mL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated. Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity. |
100% | With potassium carbonate In acetonitrile at 76℃; for 74h; | 1.1a 1a) Synthesis of 1-(5-benzyloxytetralin-6-yl)ethanone (1) 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (300 mL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated. Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity. |
100% | With potassium carbonate In acetonitrile at 76℃; for 74h; | 1.1a 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (300 mL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated. (0082) Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity. |
100% | In acetonitrile at 76℃; for 74h; | 1.a la) Synthesis of l-(5-benzyloxytetralin-6-yl)ethanone (1) 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (300 mL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated. Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity. |
100% | With potassium carbonate In acetonitrile at 76℃; for 74h; | 1.1a la) Synthesis of l-(5-benzyloxytetralin-6-yl)ethanone (1) 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (300 mL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated. Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity. |
100% | With potassium carbonate In acetonitrile at 76℃; for 122h; | 1.a la) Synthesis of l-(5-benzyloxytetralin-6-yl)ethanone (1) 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (BOO imL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated. Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity. |
With potassium carbonate In acetonitrile at 76℃; for 48h; | 1.1a 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (300 mL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated.Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 100 percent / pyridine / CH2Cl2 / 3 h 2: 100 percent / aluminum chloride / 1,2-dichloro-benzene / 12 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 2: KOH; pyridine 3: acetic acid; aqueous hydrochloric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 2: KOH; pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: Methyltriphenylphosphonium bromide With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 1-(1-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one In tetrahydrofuran at 0 - 20℃; for 72h; Inert atmosphere; | |
58% | Stage #1: Methyltriphenylphosphonium bromide With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 1-(1-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one In tetrahydrofuran at 0 - 20℃; for 72h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 1.2: 72 h / 0 - 20 °C / Inert atmosphere 2.1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate / acetonitrile / 16 h / 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With aluminum (III) chloride at 135℃; for 1h; | 20 General procedure: To a flask containing 2,3-dimethylphenyl acetate (1.85 g, 1 1.27 mmol, 1.0 eq.), AlC (1.73 g, 16.90 mmol, 1.5 eq.) was added portionwise. The reaction was continued at 135°C for 1 h. The resulting solid was then hydrolyzed with a mixture of ice and diluted HCI aqueous solution and extracted with AcOEt three times. Organic layers were combined, washed with diluted NaOH aqueous solution, dried, filtered off and concentrated in vacuo. The oily residue was purified by FCC (SiHP, Hexane: AcOEt 4:1) to afford the title compound (1.40 g, 8.53 mmol, yield 76%) as a white solid. ESI-MS: 165 [M+H]+ 1H NMR (300 MHz, DMSO-ofe) d 12.71 (s, 1H), 7.68 (d, J= 8.2 Hz, 1H), 6.80 (d, J= 8.2 Hz, 1H), 2.61 (s, 3H), 2.28 (s, 3H), 2.09 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C | ||
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C | ||
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / 0 °C 3.2: 3 h / 0 - 20 °C |
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C | ||
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C | ||
Multi-step reaction with 3 steps 1.1: acetonitrile / 74 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C | ||
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 122 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / -16 - 20 °C | ||
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C | ||
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / 0 °C 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 4.2: 0 - 5 °C |
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C | ||
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C | ||
Multi-step reaction with 4 steps 1.1: acetonitrile / 74 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C | ||
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 122 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C | ||
Multi-step reaction with 5 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / 0 °C 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 4.2: 0 - 5 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C | ||
Multi-step reaction with 5 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C |
Multi-step reaction with 5 steps 1.1: acetonitrile / 74 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 5.2: Cooling with ice | ||
Multi-step reaction with 5 steps 1.1: potassium carbonate / acetonitrile / 122 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 6.1: potassium carbonate / acetic acid butyl ester; water / 0.58 h / 100 °C | ||
Multi-step reaction with 5 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 5.2: 50 - 80 °C | ||
Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / 0 °C 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 4.2: 0 - 5 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 6.1: potassium carbonate / water; isopropyl alcohol / 50 - 80 °C / pH Ca. 8 - 12 |
Multi-step reaction with 5 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 5.2: 3 h / 50 °C / pH Ca. 12 | ||
Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 6.1: potassium carbonate / isopropyl alcohol; water / 3 h / 50 - 80 °C / pH Ca. 8 - Ca. 12 | ||
Multi-step reaction with 6 steps 1.1: acetonitrile / 74 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 5.2: Cooling with ice 6.1: potassium carbonate / isopropyl alcohol; water / 3 h / 50 - 80 °C / pH 8 - 12 | ||
Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile / 122 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 6.1: potassium carbonate / isopropyl alcohol; water / 3 h / 50 °C / pH Ca. 8 - Ca. 12 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C | ||
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium carbonate In acetonitrile at 76℃; for 48h; | 1.1a Example 1: Synthesis of the monohydrate potassium salt of formula (I) la) Synthesis of l-(5-benzyloxytetralin-6-yl)ethanone ( 1 ) 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (300 mL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated. (0168) Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C | ||
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C | ||
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C |
Multi-step reaction with 2 steps 1.1: acetonitrile / 74 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C | ||
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 122 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: tetrahydrofuran / 20 °C / Cooling with ice 2: triethylsilane; trifluoroacetic acid / dichloromethane / 0 - 20 °C 3: pyridine / dichloromethane / 0 - 20 °C 4: sodium azide / acetone / 12 h / 20 °C 5: C19H19Cl3CoNO; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / 12 h / 60 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 20 °C / Cooling with ice 2: triethylsilane; trifluoroacetic acid / dichloromethane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: tetrahydrofuran / 20 °C / Cooling with ice 2: triethylsilane; trifluoroacetic acid / dichloromethane / 0 - 20 °C 3: pyridine / dichloromethane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: tetrahydrofuran / 20 °C / Cooling with ice 2: triethylsilane; trifluoroacetic acid / dichloromethane / 0 - 20 °C 3: pyridine / dichloromethane / 0 - 20 °C 4: sodium azide / acetone / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at 20℃; Cooling with ice; |
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