| 94% |
With sodium methylate; In methanol; for 24h;Heating / reflux; |
Following the disclosure provided in U. S. Patent No. 5,760, 068, 4'-Methylacetophenone (5.26 g, 39.2mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCI was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried overMgS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
| 94% |
|
Following the disclosure provided in U. S. Patent No. 5,760, 068,4'- Methylacetophenone (5. 26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5. 5 mL (46.2 mmbl) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCI was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MgS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
| 94% |
|
Step 1: Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione. Following the disclosure provided in U.S. Pat. No. 5,760,068, 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
| 94% |
|
Step 1: Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione. Following the disclosure provided in U.S. Pat. No. 5,760,068, 4'-methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
| 94% |
|
Following the disclosure provided in U. S. Patent No. 5,760, 068, 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCI was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MgS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
| 94% |
|
Step 1: Preparation of 1- (4-METHYLPHENYL)-4, 4,4- trifluorobutane-1, 3-dione. [000201] Following the disclosure provided in U. S. Patent No. 5,760, 068, 4'-Methylacetophenone (5.26 g, 39.2 MMOL) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 MMOL) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 MMOL) ETHYL TRIFLUOROACETATE was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCI was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MGS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
| 94% |
|
Following the disclosure provided in U. S. Patent No. 5,760, 068, 4'-Methylacetophenone (5.26 g, 39.2 MMOL) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 MMOL) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCI was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MGS04, FILTERED and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
| 94% |
|
Following the disclosure provided in U. S. Patent No. 5,760, 068, 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCI was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MgS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
| 94% |
|
4'-methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MgS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
| 94% |
|
4'-methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MgS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
| 94.8% |
With sodium methylate; In toluene; at 20 - 30℃; for 5h; |
In a 1000 ml reaction flask, add 500.0 g of toluene and 187.9 g (1.40 mol)P-methylacetophenone, 94.1 g of sodium methoxide (1.68 mol), slowly dropwise add 238.8 g of ethyl trifluoroacetate (1.54 mol), and keep it at 20-30 C. After the dropwise addition, continue to react for 5 hours. A good 5N hydrochloric acid solution is used to adjust the pH to 2, and then washed twice with 500 g of purified water; the washed organic phase is slowly cooled to -10 C to -5 C, crystallized for 2 hours, and filtered and dried to obtain 305.5 g of light yellow. Solid, molar yield 94.8%, purity 99.8%. |
| 89% |
|
(1) To a 100 mL round bottom flask was added 14.9 mmol of 4-methylacetophenone (Compound 3b)Dry THF 30 mL,Cooling to -5 ~ 0 ,NaH 0.715 g (29.8 mmol) was added portionwise under nitrogen,Stir at this temperature for 30 min,Was added 3.175 g (22.4 mmol) of ethyl trifluoroacetate,The reaction was stirred at room temperature for 6 h,The solvent was distilled off under reduced pressure, diluted with ice water,The pH of the solution was adjusted to 6 with 1 mol / L HCl,The organic layer was washed with 5 mL of water and dried over anhydrous magnesium sulfate. The solvent was dried and the concentrated product was dried. The organic layer was washed with 5 mL of water,To give compound 4b (4,4,4-trifluoro-1- (4-methylphenyl) -1,3-butanedione) in 89% yield; |
| 87% |
|
25% sodium methoxide in methanol (51.3 ml, 223.5 mmol) and ethyl trifluoroacetate (24.4 ml, 204.9 mmol) were dissolved in 110 mL methyl tert-butyl ether under N2, at room temperature. 4'-methyl acetophenone (25.0 ml, 186.3 mmol) was added and stirred at room temperature overnight. The reaction was washed with 3M HC1 and dried over magnesium sulfate. The solution was then evaporated and the resulting oil dried under vacuum overnight. The resulting light orange crystalline solid was washed with cold isooctane and dried under vacuum to yield an off white crystalline solid (37.3 g, 87% yield). LC tr=3.49 minutes (C- 18 column, 5 to 95% acetonitrile/water over 6 minutes at 1.7 mL/min with detection 254 nm, at 23 C). |
| 87.3% |
|
Will p-methyl acetophenone (0.67g, 5mmol)Soluble in 20mL dry THF,NaH (0.24 g, 10 mmol) was added at 0C.Stir for 10 min.Adding ethyl trifluoroacetate under N2 protection(0.9 mL, 7.5 mmol) into the reaction solution,The drop was transferred to room temperature and the reaction was continued for 12 h.After the reaction was completed, it was quenched with saturated aqueous sodium bicarbonate (50 mL).And extracted with ethyl acetate (50 mL x 3).Combine the organic phase,Dry, concentrate.The crude product was purified by column chromatography to give 1 g of a yellow solid.Yield 87.3%. |
| 86% |
With sodium; In methanol; for 24h;Reflux; |
Add 4.5 g of metallic sodium to 70 ml of anhydrous methanol.After the reaction is completed, it is cooled to room temperature.Slowly add p-methylacetophenone 13.5g (100mmol)And ethyl trifluoroacetate 17g (120mmol), after the addition is completed,The mixture was heated to reflux for 24 hours and concentrated to a yellow viscous liquid.Add 2mol/L hydrochloric acid to adjust the pH to 2~3, extract with ethyl acetate.Drying with magnesium sulfate,The solvent was evaporated to give a yellow oil, 1-p-tolyl-4,4,4-trifluorobutane-1,3dione, 20 g, yield 86%. |
| 85% |
|
Intermediate 10: 4,4,4-trifluoro-1-(p-tolyl)butane-1,3-dione To a solution of MeONa prepared from sodium (1.919 g, 83.0 mmol) and methanol (60 mL) was added ethyl 2,2,2-trifluoroacetate (ALDRICH, 8.19 ml_, 54.8 mmol) and the reaction was stirred at rt 30 min. Then 1-(p-tolyl)ethanone (ALDRICH, 6.97 mL, 52.2 mmol) was added, the reaction mixture was heated at 60C overnight. The reaction was checked by LCMS and the end of the reaction was observed. The reaction mixture was concentrated under vacuum and partitioned between sodium carbonate (10%) 25 mL and DCM (25 mL), the organic layer was separated, dried over Na2S04, filtered and concentrated under vacuum to afford a brown solid (10.2 g, 44.3 mmol, 85%). 1H NMR (400 MHz, CDCI3) delta ppm: 7.85 (d, 2H), 7.30 (d, 2H), 6.56 (s, 1 H), 2.45 (s, 3H). |
| 85% |
|
To a solution of MeONa prepared from sodium (1.919 g, 83.0 mmol) and methanol (60 mL) was added ethyl 2,2,2-trifluoroacetate (ALDRICH, 8.19 mL, 54.8 mmol) and the reaction was stirred at rt 30 min. Then 1-(p-tolyl)ethanone (ALDRICH, 6.97 mL, 52.2 mmol) was added, the reaction mixture was heated at 60 C. overnight. The reaction was checked by LCMS and the end of the reaction was observed. The reaction mixture was concentrated under vacuum and partitioned between sodium carbonate (10%) 25 mL and DCM (25 mL), the organic layer was separated, dried over Na2SO4, filtered and concentrated under vacuum to afford a brown solid (10.2 g, 44.3 mmol, 85%). 1H NMR (400 MHz, CDCl3) delta ppm: 7.85 (d, 2H), 7.30 (d, 2H), 6.56 (s, 1H), 2.45 (s, 3H). |
| 8.47 g (94%) |
With hydrogenchloride; In methanol; |
Step 1: Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione. Following the disclosure provided in U.S. Pat. No. 5,760,068, 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was.stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
| 8.47 g (94%) |
With hydrogenchloride; In methanol; |
Step 1: Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione. Following the disclosure provided in U.S. Pat. No. 5,760,068, 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
| 8.47 g (94%) |
With hydrogenchloride; In methanol; |
Step 1 Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione Following the disclosure provided in U.S. Pat. No. 5,760,068, 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
|
With hydrogenchloride; sodium methylate; In methanol; |
Step a 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione 4'-Methylacetophenone was dissolved in methanol (25 ml) under nitrogen atmosphere. To the stirred solution was added 25% sodium methoxide in methanol (12 ml). The reaction mixture was stirred for 5 minutes and ethyltrifluoroacetate (5.5 ml) was added. After refluxing under nitrogen atmosphere for 24 hours the mixture was cooled to room temperature and concentrated. 10% hydrochloric acid (100 ml) was added. The mixture was extracted with ethyl acetate (4*75 ml). The combined organic layer was dried over MgSO4, filtered and concentrated. The product was obtained as an oily residue. |
| 8.47 g (94%) |
With hydrogenchloride; In methanol; |
Step 1 Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
| 8.47 g (94%) |
With hydrogenchloride; In methanol; |
Step 1: Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
| 8.47 g (94%) |
With hydrogenchloride; In methanol; |
Step 1: Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione. Following the disclosure provided in U.S. Pat. No. 5,760,068, 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
|
With sodium methylate; In methanol; toluene; at 25 - 60℃; |
Stage-1:Preparation of l-(4-methylphenyl)-4,4,4-trifluorobutane-l,3-dione (IV)4-Methylacetophenone (50 g, 0.373 mol) was dissolved in toluene (250 ml) and 30% methanolic sodium methoxide solution (80.6 g, 0.447 mol), followed by 1- ethyltrifluoro acetate (63.58 g, 0.447 mol) were added at 25-3O0C. Temperature of the reaction mass was raised to 55-600C and stirred ~ 4 hr to complete the reaction. The reaction mass was cooled to 20-250C and washed with 10% aqueous hydrochloric acid (200 ml). The layers were separated and concentrated the organic layer at 50-550C under reduced pressure to produce 80 g of l-(4-methylphenyl)-4,4,4-trifluoiObutane- 1,3-dione (IV) as an oily mass. |
|
|
General procedure: Substituted acetophenone 1 (149 mmol) was dissolved in dry THF (300 mL) under nitrogen atmosphere and NaH (7.15 g, 298 mmol) was added in portions maintaining the temperature between -5 and 0 C. After stirring at this temperature for 30 min, ethyl trifluoroacetate (31.75 g, 224 mmol) was added and the reaction mixture was allowed to stir at room temperature for 6 h. The reaction mixture was evaporated, added with ice-water, acidified with HCl (1 N) to pH 6, and extracted with EtOAc (3 × 100 mL). The combined organic layer was washed with water (50 mL), dried over MgSO4, and concentrated. The solid residue was washed with hexane and dried under high vacuum to provide a solid mass, which was re-dissolved in CH2Cl2, and dried under high vacuum to give a white solid diketone 2 in 92 +/- 2% (n = 3) yield, Rf = 0.22-0.25 (25% EtOAc/Hexanes). |
|
|
General procedure: Step a. To a suspension of ethyl trifluoroacetate (850 mg, 6 mmol, 1.2 equiv) and NaH (150 mg, 6.25 mmol, 1.25 equiv) in anhydrous THF, individual ketone substrates (5 mmol, 1 equiv) in anhydrous THF were slowly added at 25 C. The resulting mixture was stirred for 5 h, concentrated, diluted with ethyl acetate, washed, in tandem, with water, 1 N HCl and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc-hexane, 1:4) to afford pure 1,3-diketone in fair to good yields. |
|
With sodium methylate; In methanol; for 2h;Reflux; |
General procedure: Referring to Scheme 1, to the appropriate acetophenone derivative (0.05 mol) and ethyltrifluoroacetate (0.075 mol) in methanol (20 mL), sodium methoxide solution (0.1 mol of Na + 15 mL ofCH3OH) was added dropwise at room temperature, and the mixture was refluxed for 2 h. After themethanol was evaporated under vacuum, the residue was dissolved in ethyl acetate (50 mL), washedwith 5% HCl (25 mL) and water (25 mL), and dried over sodium sulfate. After the solvent wasevaporated under vacuum, the corresponding compound II was obtained. |
| 63.5 g |
With sodium; In ethanol; toluene; at 100℃; for 4h; |
Sodium metal (6.9g, 0.3mol) and toluene (150 mL) made of an off-white suspension, was added absolute ethanol (20 mL), at 65 C for 1 hour, cooled to room temperature. Added p-methylacetophenone (40.2g, 0.3mmol) and ethyl trifluoroacetate (60mL, 0.6mmol), was slowly warmed to 100 C for 4 hours. Toluene was evaporated, and the residue was added to a mixture of ice and glacial acetic acid (containing 33% glacial acetic acid), and extracted four times with ethyl acetate. The combined extracts were washed with water, dried over anhydrous sodium sulfate, the solvent was evaporated to obtain a brown solid 63.5g. |
|
With sodium methylate; In methanol; isopropyl alcohol; at 50℃; for 4h; |
In a 250 mL three-necked glass flask, p-methylacetophenone (10 g, 0.075 mol) and ethyl trifluoroacetate(13.7 g, 0.096 mol), 18.2 g of sodium methoxide in methanol (25% concentration) and 20 mL of isopropanol were added and the temperature was raised to 50 C, after holding for 4 h, the temporary solution for the reaction a. |
|
|
A solution of 27 p-methylacetophenone (0.67g, 5mmol) in dry 28 THF (20mL) was added dropwise to 29 NaH (0.24g, 10mmol) in dry THF (50mL) under nitrogen atomosphere and the mixture was stirred for 1h at 0C. Then a solution of 30 ethyl trifluoroacetate (0.9mL, 7.5mmol) in dry THF (10mL) was added dropwise. The mixture was warmed to room temperature for 12h. The reaction was quenched with saturation NaHCO3 and extracted with ethyl acetate (50mL×3). The combined organic extracts were washed with brine (50mL), dried with Na2SO4 and evaporated. Finally, the resulting residue was purified by column chromatography on silica gel as indicated to give 6a as canary yellow solid. (0015) To a solution of 6a (0.46g, 2mmol) in 31 ethyl alcohol (50mL) was added 32 4-hydrazinyl-N-hydroxybenzamide hydrochloride (0.53g, 2.6mmol). Then the temperature was raised to 70C for 5h. The mixture solution was concentrated to dryness, added 33 water (50mL) and extracted with ethyl acetate (30mL×3). The combined organic extracts were washed with brine (30mL), dried with Na2SO4 and concentrated. Finally, the resulting residue was purified by column chromatography on silica gel as indicated to give 7 as white solid. (0016) To a solution of 7 (0.36g, 1mmol) in 34 methyl alcohol (30mL) were added 1M aqueous solution of 35 NaOH (3mL) and 36 NH2OH (50wt% in water, 3mL) dropwise successively at 0C. The reaction was warmed to room temperature for 3h. The mixture solution was concentrated to dryness, and the obtained solid was dissolved in water. The pH was adjusted to 7 with 1M aqueous solution of 37 HCl. The resulting precipitate was filtered to give 38 8 as white solid. Yield: 63.2%. Mp: 104.5-105.9C. ESI-MS: m/z, 360.3 [M-H]-. 1H NMR (600MHz, DMSO-d6) delta: 11.33 (s, 1H), 9.13 (s, 1H), 7.80 (d, J=8.6 Hz, 2H), 7.42 (d, J=8.6 Hz, 2H), 7.21-7.18 (m, 4H), 7.17 (s, 1H), 2.30 (s, 3H). 13C NMR (151MHz, DMSO) delta: 145.19, 140.87, 139.03, 132.90, 129.56, 129.43, 128.77, 128.00, 126.86, 125.60, 125.54, 105.91, 20.86. HRMS (ESI+) m/z calcd for C18H14F3N3O2 [M-H]- 360.1038, found: 360.1047. |
|
|
Following the disclosure provided in U. S. Patent No. 5,760, 068, 4'-Methylacetophenone (5.26 g, 39.2 MMOL) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 MMOL) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 MMOL) ethyl TRIFLUOROACETATE was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCI was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MGS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification. |
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