* 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.
iv) A solution of 2-[2-methyl-3-(methoxymethyleneoxy)-phenyl]-1,3-dioxane (0.65 g, 2.73 mmol) in a mixture of THF:5M HCl (1:1) (50 ml) was stirred at ambient temperature for 20 hours. The reaction mixture was diluted with water (50 ml) and extracted with ethyl acetate (3*). The combined organic extracts were washed wih (1) water, (2) saturated brine, dried over magnesium sulphate, filtered and evaporated in vacuo to give 2-methyl-3-hydroxybenzaldehyde as a white solid.
3
[ 90111-15-2 ]
[ 79-44-7 ]
2-methyl-3-(diethylaminocarbonyloxy)benzaldehyde[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In pyridine;
i) A mixture of <strong>[90111-15-2]2-methyl-3-hydroxybenzaldehyde</strong> (synthesised by the methods of Example 20 (i)-(iv)) (2.35 g, 17.3 mmol) and dimethylcarbamoyl chloride (2.7 ml, 21.5 mmol) in dry pyridine (30 ml) was stirred at 90 C. for 16 hours. The reaction mixture was cooled, poured into water (200 ml) and extracted with ethyl acetate (3*). The combined organic extracts were washed with (1) water, (2) saturated brine, dried over magnesium sulphate, filtered and evaporated in vacuo to give an amber oil (3.60 g, 89%). The crude oil was purified by flash chromatography on silica (eluant hexane:diethyl ether=1:1) to give 2-methyl-3-(diethylaminocarbonyloxy)benzaldehyde as a mobile yellow oil.
(b) 3-(2-aminoethyl)-4-methyl-5-n-propyloxyindole oxalate Sodium hydride (1.15 g, 50% in oil) was added to a stirred solution of <strong>[90111-15-2]2-methyl-3-hydroxybenzaldehyde</strong> (3.00 g) in dry DMF (30 ml). The mixture was stirred for 1 h at room temperature under nitrogen, then n-propyl iodide (4.49 g) was added portionwise over 20 min, followed by stirring for 1 h. The mixture was poured into water and extracted with diethyl ether, and the combined extracts dried (MgSO4) and evaporated to dryness. Purification by chromatography (SiO2; hexane/ethyl acetate) gave 2-methyl-3-n-propyloxybenzaldehyde (1.38 g).
2-methyl-3-(m-fluorophenyl)sulfonyloxybenzaldehyde[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
34.0%
With triethylamine; In dichloromethane; at 0 - 20℃; for 8.5h;
Compound A (see Document Tetrahedron, 2012,68 (11), 2509-2512 Preparation method) 1.36g (10mmol) with 30mlCH2Cl2 in 100ml round bottom flask, at 0 deg. C was slowly added 1.21g (12mmol) of triethylamine, after stirring for 30min, at the same conditions was slowly added dropwise at between 0 deg. C fluorobenzenesulfonyl chloride 2.13g (11mmol), after the addition is complete, slowly warm to room temperature, the reaction 8h, followed by addition of 200ml of ice water the reaction liquid dispersion, CH2Cl2 layer was collected, washed three times with saturated brine, the organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product E, the above crude product with 20ml of ethyl acetate recrystallization purified product B 1.0g (yield: 34.0%).
General procedure: To a solution of the hydroxy-methylbenzaldehyde (34 mg,0.25 mmol) in anhydrous DMF (6.0 mL), K2CO3 (35 mg,0.25 mmol) was added and the mixture was stirred at room temperaturefor 30 minutes. Then, methyl iodide (30 muL, 68 mg,0.5 mmol) was added and the reaction was stirred at room temperatureovernight. The reaction was quenched by the additionof distilled water, and the aqueous phase was extracted threetimes with ethyl acetate. The combined organic phases weredried with MgSO4 and concentrated in vacuo. The residue waspurified by column chromatography on silica gel.
methyl 4-(3-formyl-2-methylphenoxy)-3-methylbenzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
29%
With pyridine; potassium carbonate; copper(II) oxide; for 38.0h;Inert atmosphere; Reflux;
To a solution of methyl 4-bromo-3-methylbenzoate (S15) (202 mg, 881 mumol, 1.2 equiv) and <strong>[90111-15-2]3-hydroxy-2-methylbenzaldehyde</strong> (S16) (100 mg, 734 mumol, 1 equiv) in dry pyridine (2.0 mL) were added K2CO3 (203 mg, 1.47 mmol, 2.0 equiv) and CuO (146 mg, 1.84 mmol, 2.5 equiv) at room temperature under an argon atmosphere. After being stirred at reflux for 38 h, the reaction mixture was cooled to room temperature and filtered through a pad of Celite. The filtrate was concentrated in vacuo, and the resulting residue was purified by flash column chromatography on silica gel (eluted with hexane/EtOAc = 9:1) to afford the diphenyl ether S17 (61.0 mg, 215 mumol, 29%) as an colorless oil.
With potassium carbonate; In acetonitrile; at 60℃; for 5.0h;
To a stirred mixture of <strong>[90111-15-2]3-hydroxy-2-methylbenzaldehyde</strong>(500 mg, 3.67 mmol, 1 equiv.) and iodoethane (1145.5 mg, 7.34 mmol, 2.00 equiv.) in CH3CN(10 mL) was added K2CO3(761.3 mg, 5.51 mmol, 1.50 equiv.) at room temperature. The resulting mixture was stirred for 5 h at 60 degrees C. The reaction was monitored by LCMS. The resulting mixture was concentrated under reduced pressure. The resulting mixture was extracted with EtOAc (3 x 250 mL). The combined organic layers were washed with brine (3 x 250 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by Prep- TLC (PE/EtOAc 5:1) to afford 3-ethoxy-2-methylbenzaldehyde (370 mg) as a light yellow oil.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
