* 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.
o-Chlorotoluene (1.89 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol percent) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 82 mg ethyl o-chlorophenylacetate was obtained by column chromatography, in a yield of 83percent. 1HNMR (400 MHz, CDCl3) δ 1.24 (t, J=7.2 Hz, 3H), 3.77 (s, 2H), 4.15 (q, J=7.2 Hz, 2H), 7.21-7.24 (m, 2H), 7.28-7.30 (m, 1H), 7.36-7.40 (m, 1H); 13CNMR (100 MHz, CDCl3) δ 14.2, 39.2, 61.0, 126.9, 128.6, 129.5, 131.4, 132.6, 134.6, 170.6; HRMS (ESI) calcd. for C10H11ClNaO2 [M+Na]: 221.0340. found: 221.0343. The ethyl o-chlorophenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 66 mg product o-chlorophenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 94percent.
Reference：
[1] Patent: US2013/303798, 2013, A1, . Location in patent: Paragraph 0066; 0067
[2] Journal of the American Chemical Society, 2012, vol. 134, # 24, p. 9902 - 9905
2
[ 2444-36-2 ]
[ 64-17-5 ]
[ 40061-54-9 ]
Yield
Reaction Conditions
Operation in experiment
97%
Reflux
Intermediate AR(1)ethyl 2-(2-chlorophenyl)acetateA mixture of 2-(2-chlorophenyl)acetic acid (10 g, 58.6 mmol) in EtOH (Volume: 152 ml) was treated with H2S04 (1.719 ml, 32.2 mmol). The result mixture was refluxed overnight. The heat was removed, and the reaction mixture was concentrated. The resulting oil was dissolved in EtOAc and CAREFULLY treated with aqueous Na2C03 (3.47 g, 32.8 mmol) (CAUTION: Gas evolution) until the solution remained basic and no further gas evolution was seen. The EtOAc layer was then removed and the aqueous layer was again extracted two times with EtOAc. The combined organic layers were then washed with brine, dried over Na2S04 and concentrated in vacuo to obtain ethyl 2-(2- chlorophenyl)acetate (1 1.32 g, 57.0 mmol, 97 percent yield). LC-MS (M+H)+ = 199.1.3/4 NMR (500MHz, CD3OD) δ 7.41 (ddd, J=16.8, 5.6, 3.5 Hz, 1H), 7.35 (dd, J=5.5, 3.7 Hz, 1H), 7.28 (dd, J=5.8, 3.7 Hz, 2H), 4.17 (q, J=7.0 Hz, 2H), 3.80 (s, 2H), 1.26 (t, J=7.2 Hz, 3H).
Reference：
[1] Patent: WO2012/103297, 2012, A1, . Location in patent: Page/Page column 195-196
[2] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 4, p. 1586 - 1605
[3] Australian Journal of Chemistry, 2013, vol. 66, # 8, p. 864 - 873
[4] Journal of Medicinal Chemistry, 1993, vol. 36, # 26, p. 4239 - 4249
[5] Chinese Journal of Chemistry, 2010, vol. 28, # 4, p. 605 - 612
[6] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1263 - 1266
[7] Synthesis (Germany), 2015, vol. 47, # 13, p. 1913 - 1921
3
[ 694-80-4 ]
[ 681-94-7 ]
[ 40061-54-9 ]
Reference：
[1] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 11, p. 3383 - 3384
Intermediate AR(1)ethyl 2-(2-chlorophenyl)acetateA mixture of 2-(2-chlorophenyl)acetic acid (10 g, 58.6 mmol) in EtOH (Volume: 152 ml) was treated with H2S04 (1.719 ml, 32.2 mmol). The result mixture was refluxed overnight. The heat was removed, and the reaction mixture was concentrated. The resulting oil was dissolved in EtOAc and CAREFULLY treated with aqueous Na2C03 (3.47 g, 32.8 mmol) (CAUTION: Gas evolution) until the solution remained basic and no further gas evolution was seen. The EtOAc layer was then removed and the aqueous layer was again extracted two times with EtOAc. The combined organic layers were then washed with brine, dried over Na2S04 and concentrated in vacuo to obtain ethyl 2-(2- chlorophenyl)acetate (1 1.32 g, 57.0 mmol, 97 % yield). LC-MS (M+H)+ = 199.1.¾ NMR (500MHz, CD3OD) delta 7.41 (ddd, J=16.8, 5.6, 3.5 Hz, 1H), 7.35 (dd, J=5.5, 3.7 Hz, 1H), 7.28 (dd, J=5.8, 3.7 Hz, 2H), 4.17 (q, J=7.0 Hz, 2H), 3.80 (s, 2H), 1.26 (t, J=7.2 Hz, 3H).
With thionyl chloride; at 50℃;
General procedure: A solution of 3 g (13.8 mmol) of 2-(2-bromophenyl)-acetic in 10 mL ethanol was cooled to 0 ,and 1.6 ml (22 mmol) thionylchloride was added drop wise. The reaction mixture was heated to 50 . Over night.After cooling to room temperature the solvent was removed under reduced pressure. The residue was mixed withethyl acetate and filtered over 6 g basic aluminium oxide. The filtrate was evaporated under reduced pressure. 3.5g (89%) of the ethyl 2-(2-bromophenyl)acetate (1d) were obtained.
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 8h;Heating / reflux;
Ethyl 2-(2-chlorophenyl)-2-(1H-imidazol-1-yl)acetate (26)A mixture of <strong>[40061-54-9]ethyl 2-chlorophenylacetate</strong> (2.3 g, 11.60 mmol), N- bromosuccinimmide (2.3 g, 12.81 mmol) and a catalytic amount of alpha,alpha'- azobis(isobutyronitrile) in carbon tetrachloride (27.0 ml_) was heated under reflux for 8h. The reaction mixture was cooled to room temperature and the resulting suspension was filtered over cotton. The organic filtrate was washed with 1 N solution of NaOH (3 x 5 ml_), dried over Na2SO4 and the solvent was removed. The ethyl 2-bromo-2-(2-chlorophenyl)acetate (3.2 g, 100percent) thus obtained was dissolved in acetone (40 ml_) in the presence of imidazole sodium derivative (1.04 <n="63"/>g, 11.61 mmol). The resulting yellow mixture was heated under reflux for 6h. After cooling to room temperature, H2O (10 ml_) was added. The aqueous phase was extracted with EtOAc (3 x 30 ml_) and the organic extracts were dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (ethyl acetate) to afford 26 (1.8 g, 60percent) as brownish oil. 1H-NMR (CDCI3, 200 MHz) delta 7.56 (s, 1 H), 7.46-7.42 (m, 1 H), 7.39-7.33 (m, 3H), 7.06 (s, 1 H), 6.98 (s, 1 H), 7.06 (s, 1 H), 4.28 (q, 2H, J = 7.0 Hz,), 1.26 (t, 3H, J = 7.0 Hz,); ESI MS m/z (M+1 )+ 265.
With lithium aluminium tetrahydride; In methanol; for 1h;Cooling with ice;
1. Take 100 ml of a dry single-mouth flask, and add 2-chloro-phenylacetic acid ethyl ester (1 g, 0.0054 mmol in 10 ml of methanol, then place the system in an ice bath and slowly add lithium aluminum hydride (0.41 g, 0.0108 mmol). ), continue to stir for 1 h after the additionAfter the reaction is completed, a small amount of water is added for quenching.Thereafter, methanol was removed under reduced pressure and extracted with 15 ml of ethyl acetate.After washing with saturated brine, the extract phase was collected and dried over anhydrous sodium sulfate overnight.After the end of drying, the solvent was removed under reduced pressure to give a colorless oil, Compound A,It was used directly in the next reaction without purification.
2-dimethylamino-1-methyl-1-pyrrolinium-methylsulfate[ No CAS ]
2-(α-ethoxycarbonyl-2-chlorobenzylidene)-1-methylpyrrolidine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium; In ethanol;
EXAMPLE 35 2-(alpha-ethoxycarbonyl-2-chlorobenzylidene)-1-methylpyrrolidine Follow the procedure of Example 31 to obtain 73.8 g (93percent of theory) of the title compound (b.p. 129° to 0.008 mm of Hg) from 98.4 g of 2-dimethylamino-1-methyl-1-pyrrolinium-methylsulfate, 56.1 g of <strong>[40061-54-9]2-chlorophenylacetic acid ethyl ester</strong> and a solution of 9.5 g of sodium in 190 ml of ethanol.
With hydrogenchloride; sodium bicarbonate; sodium methylate;
a. o-chlorobenzyl-(3-pyridyl)-ketone The mixture of 25.0 g (0.126 mol) of <strong>[40061-54-9]o-chlorophenylacetic acid ethyl ester</strong> and 19.0 g (0.126 mol) of nicotinic acid ethyl ester is treated in small amounts under nitrogen with 10.2 g (0.196 mol) of sodium methylate at 20°-25°C. The reaction mixture is stirred for 20 hours at 60°-70°C, in the process of which the alcohol which is formed is blown off with a weak flow of nitrogen. After the dropwise addition of 40 ml of concentrated hydrochloric acid, the bath is boiled under reflux for 18 hours, then cooled and extracted with ether. The aqueous acid phase is adjusted to pH 5 with dilute ammonia solution and ice and made alkaline with sodium hydrogen carbonate solution. The resulting suspension is extracted with ethyl acetate. The organic phase is dried over sodium sulphate and evaporated, to yield yellow crystals of o-chlorobenzyl-(3-pyridyl)-ketone (m.p. 64°-67°C).
2-(α-ethoxycarbonyl-2-chlorobenzylidene)-1-methylperhydroazepine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
EXAMPLE 49 2-(alpha-ethoxycarbonyl-2-chlorobenzylidene)-1-methylperhydroazepine Follow the procedure of Example 2 to obtain the title compound as a dark viscous oil from 80.2 g of the title compound of Example 1 and 40 g of <strong>[40061-54-9]ethyl 2-chlorophenylacetate</strong>.
With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 20℃; for 1h;
Step 4. DBU (4.1 g, 26.9 mmol, 1.2 eq) was added to a mixture of 4-(methylamino)-2-(methylthio)-pyrimidine-5-carbaldehyde (4.1 g, 22.4 mmol, 1.0 eq) and <strong>[40061-54-9]ethyl 2-(2-chlorophenyl)acetate</strong> (5.4 g, 26.9 mmol, 1.2 eq) at RT. The resulting mixture was then stirred at room temperature for 1 h, followed by addition of water and extraction with EtOAc. The combined organic layers were dried and concentrated to afford 6-(2-chlorophenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (5.0 g, 70percent in yield).
With piperidine; pyridine; hydrazine; In ethanol; water; for 3.5h;Reflux;
General procedure: Ethyl-2-arylacetate (2 mmol), aq.formaldehyde (1 mmol), aq.ammonia / aliphatic / aromatic amines (2 mmol) and a catalytic amount of piperidine and pyridine in abs. ethanol (250 mL) were refluxed for 4 hour. The course of the reaction was monitored by TLC, and after the disappearance of the starting materials, excess of alcohol is removed in vacuo and the residue extracted with benzene and washed with dil.HCl and then with water and dried. The dried benzene extract was purified by passing through a column of SiO2. The residue obtained on evaporation of the solvent, on crystallization (aq. EtOH) gave pure 3, 5-diarylpiperidin-2, 6-diones in appreciable yields (70-90percent).
With piperidine; pyridine; ammonium hydroxide; In ethanol; water; for 3.5h;Reflux;
General procedure: Ethyl-2-arylacetate (2 mmol), aq.formaldehyde (1 mmol), aq.ammonia / aliphatic / aromatic amines (2 mmol) and a catalytic amount of piperidine and pyridine in abs. ethanol (250 mL) were refluxed for 4 hour. The course of the reaction was monitored by TLC, and after the disappearance of the starting materials, excess of alcohol is removed in vacuo and the residue extracted with benzene and washed with dil.HCl and then with water and dried. The dried benzene extract was purified by passing through a column of SiO2. The residue obtained on evaporation of the solvent, on crystallization (aq. EtOH) gave pure 3, 5-diarylpiperidin-2, 6-diones in appreciable yields (70-90percent).
With piperidine; pyridine; In ethanol; water; for 4.5h;Reflux;
General procedure: Ethyl-2-arylacetate (2 mmol), aq.formaldehyde (1 mmol), aq.ammonia / aliphatic / aromatic amines (2 mmol) and a catalytic amount of piperidine and pyridine in abs. ethanol (250 mL) were refluxed for 4 hour. The course of the reaction was monitored by TLC, and after the disappearance of the starting materials, excess of alcohol is removed in vacuo and the residue extracted with benzene and washed with dil.HCl and then with water and dried. The dried benzene extract was purified by passing through a column of SiO2. The residue obtained on evaporation of the solvent, on crystallization (aq. EtOH) gave pure 3, 5-diarylpiperidin-2, 6-diones in appreciable yields (70-90percent).
With piperidine; pyridine; In ethanol; water; for 5.5h;Reflux;
General procedure: Ethyl-2-arylacetate (2 mmol), aq.formaldehyde (1 mmol), aq.ammonia / aliphatic / aromatic amines (2 mmol) and a catalytic amount of piperidine and pyridine in abs. ethanol (250 mL) were refluxed for 4 hour. The course of the reaction was monitored by TLC, and after the disappearance of the starting materials, excess of alcohol is removed in vacuo and the residue extracted with benzene and washed with dil.HCl and then with water and dried. The dried benzene extract was purified by passing through a column of SiO2. The residue obtained on evaporation of the solvent, on crystallization (aq. EtOH) gave pure 3, 5-diarylpiperidin-2, 6-diones in appreciable yields (70-90percent).
With piperidine; pyridine; In ethanol; water; for 4h;Reflux;
General procedure: Ethyl-2-arylacetate (2 mmol), aq.formaldehyde (1 mmol), aq.ammonia / aliphatic / aromatic amines (2 mmol) and a catalytic amount of piperidine and pyridine in abs. ethanol (250 mL) were refluxed for 4 hour. The course of the reaction was monitored by TLC, and after the disappearance of the starting materials, excess of alcohol is removed in vacuo and the residue extracted with benzene and washed with dil.HCl and then with water and dried. The dried benzene extract was purified by passing through a column of SiO2. The residue obtained on evaporation of the solvent, on crystallization (aq. EtOH) gave pure 3, 5-diarylpiperidin-2, 6-diones in appreciable yields (70-90percent).
With piperidine; pyridine; In ethanol; water; for 5h;Reflux;
General procedure: Ethyl-2-arylacetate (2 mmol), aq.formaldehyde (1 mmol), aq.ammonia / aliphatic / aromatic amines (2 mmol) and a catalytic amount of piperidine and pyridine in abs. ethanol (250 mL) were refluxed for 4 hour. The course of the reaction was monitored by TLC, and after the disappearance of the starting materials, excess of alcohol is removed in vacuo and the residue extracted with benzene and washed with dil.HCl and then with water and dried. The dried benzene extract was purified by passing through a column of SiO2. The residue obtained on evaporation of the solvent, on crystallization (aq. EtOH) gave pure 3, 5-diarylpiperidin-2, 6-diones in appreciable yields (70-90percent).
With piperidine; pyridine; In ethanol; water; for 4h;Reflux;
General procedure: Ethyl-2-arylacetate (2 mmol), aq.formaldehyde (1 mmol), aq.ammonia / aliphatic / aromatic amines (2 mmol) and a catalytic amount of piperidine and pyridine in abs. ethanol (250 mL) were refluxed for 4 hour. The course of the reaction was monitored by TLC, and after the disappearance of the starting materials, excess of alcohol is removed in vacuo and the residue extracted with benzene and washed with dil.HCl and then with water and dried. The dried benzene extract was purified by passing through a column of SiO2. The residue obtained on evaporation of the solvent, on crystallization (aq. EtOH) gave pure 3, 5-diarylpiperidin-2, 6-diones in appreciable yields (70-90percent).
With piperidine; pyridine; In ethanol; water; for 4.5h;Reflux;
General procedure: Ethyl-2-arylacetate (2 mmol), aq.formaldehyde (1 mmol), aq.ammonia / aliphatic / aromatic amines (2 mmol) and a catalytic amount of piperidine and pyridine in abs. ethanol (250 mL) were refluxed for 4 hour. The course of the reaction was monitored by TLC, and after the disappearance of the starting materials, excess of alcohol is removed in vacuo and the residue extracted with benzene and washed with dil.HCl and then with water and dried. The dried benzene extract was purified by passing through a column of SiO2. The residue obtained on evaporation of the solvent, on crystallization (aq. EtOH) gave pure 3, 5-diarylpiperidin-2, 6-diones in appreciable yields (70-90percent).
With di-tert-butyl peroxide; dichloro[4,5-bis(diphenylphosphino)-9,9?-dimethylxanthene]palladium(II); at 120℃; under 7600.51 Torr; for 16h;
o-Chlorotoluene (1.89 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol percent) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 82 mg ethyl o-chlorophenylacetate was obtained by column chromatography, in a yield of 83percent. 1HNMR (400 MHz, CDCl3) delta 1.24 (t, J=7.2 Hz, 3H), 3.77 (s, 2H), 4.15 (q, J=7.2 Hz, 2H), 7.21-7.24 (m, 2H), 7.28-7.30 (m, 1H), 7.36-7.40 (m, 1H); 13CNMR (100 MHz, CDCl3) delta 14.2, 39.2, 61.0, 126.9, 128.6, 129.5, 131.4, 132.6, 134.6, 170.6; HRMS (ESI) calcd. for C10H11ClNaO2 [M+Na]: 221.0340. found: 221.0343. The ethyl o-chlorophenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 66 mg product o-chlorophenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 94percent.
With water; sodium hydroxide; In 1,4-dioxane; at 60℃; for 2h;pH 10 - 14;
o-Chlorotoluene (1.89 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol percent) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 82 mg <strong>[40061-54-9]ethyl o-chlorophenylacetate</strong> was obtained by column chromatography, in a yield of 83percent. 1HNMR (400 MHz, CDCl3) delta 1.24 (t, J=7.2 Hz, 3H), 3.77 (s, 2H), 4.15 (q, J=7.2 Hz, 2H), 7.21-7.24 (m, 2H), 7.28-7.30 (m, 1H), 7.36-7.40 (m, 1H); 13CNMR (100 MHz, CDCl3) delta 14.2, 39.2, 61.0, 126.9, 128.6, 129.5, 131.4, 132.6, 134.6, 170.6; HRMS (ESI) calcd. for C10H11ClNaO2 [M+Na]: 221.0340. found: 221.0343. The <strong>[40061-54-9]ethyl o-chlorophenylacetate</strong> obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 66 mg product o-chlorophenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 94percent.
With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 48h;Inert atmosphere;
A mixture of 6-chloro-4-(ethyl amino) nicotinaldehyde (Scheme 1 compound 6) (620 mg, 3.36 mmol), ethyl 2-(2-chlorophenyl)-acetate (800 mg, 4.04 mmol) and K2CO3 (1.39 g, 10.08 mmol) in dry DMF (lOmL) was heated to 100 C under nitrogen atmosphere for 48 h. After TLC showed the starting material was completely consumed, the reaction mixture was cooled to RT, diluted with EtOAc (100 mL), washed with water (2 x 30 mL) and brine (20 mL) then dried over Na2S04 and concentrated to give a residue which was purified by flash chromatography on silica gel (eluting with petroleum ether/EtOAc 100/0 gradually increasing to 70/30) to give 7-chloro-3-(2-chlorophenyl)-l -ethyl- l,6-naphthyridin-2(lH)-one (1.10 g, 85%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): delta 8.79 (s, 1H), 8.10 (s, 1H), 7.77 (s, 1H), 7.50 (d, J= 44.7 Hz, 4H), 4.29 (m, 2H), 1.22 (t, J= 6.7 Hz, 3H). MS [ESI, MH+] = 319.04.
General procedure: To a solution of ester 8 (20 mmol) in anhydrous ethyl ether was added ethyl formate (3.2 mL,40 mmol) at 0oC. Then sodium (0.92 g, 40 mmol) was added slowly. The reaction mixture wasstirred at room temperature. After completion of the reaction, the mixture was poured into icewater and extracted with Et2O (3×30 mL). The aqueous phase was acidified with a solution of 2NHCl to PH 3. Followed an extraction with Et2O (3×30 mL) and the organic layers were combined,dried over Na2SO4, filtered and concentrated in vacuum, leading to aldehyde 9 as a yellow oil which was used in the next step without further purification. Then 9 was dissolved in anhydrousdichloromethane and p-methoxyaniline (2.95 g, 24 mmol) was added, the reaction mixture wasstirred overnight at room temperature, the solvent was evaporated and the residue was subjected tochromatography to afford -enamino ester 1.
ethyl Pyrrolo[1,2-a]quinoline-5-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
19%
With potassium phosphate; In dimethyl sulfoxide; at 150℃; for 48h;Inert atmosphere;
General procedure: A flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 °C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60?90 °C)?EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 × 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60?90°C)?EtOAc, 10:1 to 30:1] to give 3da; Yield: 16.1 mg (34percent); light yellow solid; mp 186.5?188.4 °C.
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