* 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.
Reference：
[1] Journal of Organic Chemistry, 1985, vol. 50, # 24, p. 4884 - 4888
2
[ 88867-64-5 ]
[ 23438-23-5 ]
[ 18931-78-7 ]
[ 16375-90-9 ]
[ 16375-88-5 ]
[ 98922-96-4 ]
[ 98922-97-5 ]
Reference：
[1] Journal of Organic Chemistry, 1985, vol. 50, # 24, p. 4884 - 4888
3
[ 122-85-0 ]
[ 16375-88-5 ]
Yield
Reaction Conditions
Operation in experiment
85%
With sodium tetrahydroborate In methanol at 20℃;
To a solution of 4-acetamidobenzaldehyde (10 g, 61.3 mmol) in methanol (100 mL) was added sodium borohydride (800 mg) at room temperature in portions. The reaction mixture was stirred over night, and the progress of reaction checked by TLC using 4:1 hexanes: EtOAc as eluent. Absence of starting material indicated the completion of reduction and the reaction mixture was concentrated in a rotavap. The residue was partitioned between water (25 mL) and ethyl acetate (4*50 mL) and the organic layer was washed with brine (25 mL). The ethyl acetate layer was dried over anhydrous sodium sulfate and the removal of the solvent gave the alcohol as a pale yellow solid, which was dried under high vacuum. 8.6 g (85percent); 1H NMR (DMSO-d6): δ 2.0 (s, 3H), 4.5 (d, 2H), 5.2 (t, 1H), 7.25 (d, 2H), 7.55 (d, 2H), 9.95 (s, 1H).
85%
at 20℃;
Preparation of 4-acetamidobenzyl alcohol. To a solution of 4-acetamidobenzaldehyde (10 g, 61.3 mmol) in methanol (100 mE) was added sodium borohydride (800 mg) at room temperature in portions. The reaction mixture was stirred over night, and the progress of reaction checked by TLC using 4:1 hexanes:EtOAc as eluent. Absence of starting material indicated the completion of reduction and the reaction mixture was concentrated in a rotavap. The residue was partitioned between water (25 mE) and ethyl acetate (4x50 mE) and the organic layer was washed with brine (25 mE). The ethyl acetate layer was dried over anhydrous sodium sulfate and the removal of the solvent gave the alcohol as a pale yellow solid, which was dried under high vacuum. 8.6 g (85percent); ‘H NMR (DMSO-d5): ö 2.0 (s, 3H), 4.5 (d, 2H), 5.2 (t, 1H), 7.25 (d, 2H), 7.55 (d, 2H), 9.95 (s, 1H) ppm.
61%
With ReOBr2(2-(2-hydroxy-5-methylphenyl)benzotriazole-(H))(PPh3); phenylsilane In tetrahydrofuran for 1.33333 h; Reflux
General procedure: In a typical experiment, to a mixture of carbonyl compound (1.0mmol) and [ReOBr2(hmpbta)(PPh3)] (5molpercent) in THF (3mL) at reflux temperature was added PhSiH3 (2.0mmol). The reaction mixture was stirred under air atmosphere (the reaction times are indicated in the Table 4) and the progress of the reaction was monitored by TLC or 1H NMR. Upon completion, the reaction was quenched with 1equiv of tetrabutylammonium fluoride (TBAF) (1.0M THF) during 1h. Then, the reaction mixture was evaporated and purified by silica gel column chromatography with the appropriate mixture of n-hexane and ethyl acetate to afford the alcohols, which are all known compounds.
Reference：
[1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 4, p. 676 - 681
[2] Chemical Communications, 2015, vol. 51, # 46, p. 9567 - 9570
[3] Organic Letters, 2017, vol. 19, # 13, p. 3656 - 3659
[4] Catalysis Science and Technology, 2013, vol. 3, # 1, p. 81 - 84
[5] Patent: US2007/149462, 2007, A1, . Location in patent: Page/Page column 22
[6] Patent: US9138442, 2015, B2, . Location in patent: Page/Page column 37
[7] ChemCatChem, 2017, vol. 9, # 1, p. 80 - 83
[8] Tetrahedron, 1981, vol. 37, p. 2165 - 2172
[9] Journal of the Chemical Society, Chemical Communications, 1981, # 3, p. 121 - 122
[10] Tetrahedron Letters, 2015, vol. 56, # 2, p. 414 - 418
[11] Tetrahedron, 2006, vol. 62, # 34, p. 8164 - 8168
[12] Chemistry - A European Journal, 2012, vol. 18, # 50, p. 15935 - 15939
[13] Angewandte Chemie - International Edition, 2013, vol. 52, # 19, p. 5120 - 5124[14] Angew. Chem., 2013, vol. 125, # 19, p. 5224 - 5228
4
[ 623-04-1 ]
[ 108-24-7 ]
[ 16375-88-5 ]
Yield
Reaction Conditions
Operation in experiment
98%
at 20℃; for 0.2 h; Green chemistry
General procedure: In a round-bottomed flask (25 mL) equipped with a magnetic stirrer, a mixture of aniline (0.093 g, 1 mmol) and Co3O4 (0.006 g) was prepared. Acetic anhydride (0.102, 1 mmol) was then added to the reaction mixture and stirring was continued at room temperature for 3 min. The progress of the reaction was followed by TLC. After the reaction completion, the products was extracted with EtOAc and filtered to remove Co3O4. The organic solvent was then washed with H2O (2 x 10 mL) and saturated NaHCO3 solution and then dried over anhydrous Na2SO4. The solvent was removed under vacuum to afford the pure product.
91%
at 20℃; for 0.1 h;
General procedure: Alcohol, phenol, and/or amine (1 mmol) were added to amixture of the ZnAl2O4SiO2 nanocomposite (100 mg) andacetic anhydride (1 mmol). The mixture was stirred at 75 °C(for alcohols and phenols) or at room temperature (for amines)for a time. The progress of the reaction was monitored by TLCand/or GC‐MS. When the reaction was completed, ethyl acetate(10 mL) was added and the mixture was filtered to separate offthe catalyst. The catalyst was washed twice with 7.5 mL ethylacetate. The combined organic phases were washed with a10percent solution of NaHCO3 and then dried over MgSO4. The solventwas removed to yield the product. If further purificationwas needed, the product was passed through a short column ofsilica gel. All products were characterized on the basis ofGC‐MS, FT‐IR, and 1H‐NMR spectral data by comparing thesespectra with those of standard samples or literature data.
91%
at 50℃; for 0.15 h;
General procedure: In a round-bottom flask (10 mL) equipped with a magnetic stirrer, a mixture of PhNH2(1 mmol, 0.093 g) and H2O(3 mL) in oil bath (50 °C) was prepared. Magnetically recyclable nanoparticles of Fe3O4/Cu (0.05 mmol) was then added, and the mixture was stirred for 1 min under oil bath conditions. Addition of Ac2O(1 mmol, 0.102 g) to the prepared mixture was followed by stirring for 3 min at 50 °C. After completion of the reaction, the copper nanocatalyst was separated by an external magnet and the mixture was extracted with EtOAc (3 × 8 mL). Organic layers were then dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure affords the pure acetanilide in 95percent yield (0.128 g, Table 2, entry 1).
Reference：
[1] Research on Chemical Intermediates, 2017, vol. 43, # 1, p. 413 - 422
[2] Chinese Journal of Catalysis, 2014, vol. 35, # 3, p. 368 - 375
[3] Journal of the Iranian Chemical Society, 2017, vol. 14, # 11, p. 2467 - 2474
[4] Applied Catalysis A: General, 2010, vol. 382, # 2, p. 293 - 302
[5] Journal of the Iranian Chemical Society, 2014, vol. 11, # 4, p. 1103 - 1112
[6] Journal of Organic Chemistry, 2001, vol. 66, # 26, p. 8815 - 8830
[7] Journal of Organic Chemistry, 2012, vol. 77, # 21, p. 9553 - 9561
[8] Journal of Organic Chemistry, 2018, vol. 83, # 5, p. 2542 - 2553
[9] Chemistry of Materials, 2011, vol. 23, # 21, p. 4844 - 4856
[10] Journal of the American Chemical Society, 2016, vol. 138, # 17, p. 5568 - 5575
With ammonium hydroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; In ethanol; at 50℃; for 24h;
General procedure: Under an air atmosphere, a Schlenk tube was charged with MCM-41-bpy-CuI (40 mg, 0.025 mmol), alcohol (0.5 mmol), TEMPO (4 mg, 0.025 mmol), aqueous ammonia (0.5 mmol, 25e28%, w/w) and EtOH (1.0 mL). The mixture was stirred at 50 C for 18-48 h. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate (10 mL), and filtered. The MCM-41-bpy-CuI complex was washed with EtOH (2*5 mL), and Et2O (5 mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (petroleum/ethyl acetate=15:1 to 10:1) to provide the desired product.
86%Spectr.
With bismuth vanadate; oxygen; In acetonitrile; at 40℃; under 760.051 Torr; for 3h;Schlenk technique; Irradiation;
General procedure: Bismuth vanadate (32.3 mg, 100 mmol) was added to a Schlenkflask containing benzyl alcohol stock solution (1 mL, 0.1 mmol inacetonitrile) and acetonitrile (9 mL). The mixture was left to stirfor 30 min to disperse the catalyst under a dioxygen atmospherevia a balloon. The mixture was then irradiated with a 30W blueLED array at a distance of 2 cmwith an irradiance of 245mWcm2.The mixture reached ca. 40 C by the end of the reaction and afterirradiation, the catalyst was removed using centrifugation at4000 rpm for 30 min. For GC analysis, 1 mL of supernatant wastaken and 1 lL injected. For NMR analysis, the supernatant wasreduced in volume using a rotary evaporator at 65 mbar at 20 C,and the residue dissolved in d6-DMSO containing maleic acid asan internal standard.
With sodium tetrahydroborate; In methanol; at 20℃;
To a solution of 4-acetamidobenzaldehyde (10 g, 61.3 mmol) in methanol (100 mL) was added sodium borohydride (800 mg) at room temperature in portions. The reaction mixture was stirred over night, and the progress of reaction checked by TLC using 4:1 hexanes: EtOAc as eluent. Absence of starting material indicated the completion of reduction and the reaction mixture was concentrated in a rotavap. The residue was partitioned between water (25 mL) and ethyl acetate (4*50 mL) and the organic layer was washed with brine (25 mL). The ethyl acetate layer was dried over anhydrous sodium sulfate and the removal of the solvent gave the alcohol as a pale yellow solid, which was dried under high vacuum. 8.6 g (85%); 1H NMR (DMSO-d6): delta 2.0 (s, 3H), 4.5 (d, 2H), 5.2 (t, 1H), 7.25 (d, 2H), 7.55 (d, 2H), 9.95 (s, 1H).
85%
With methanol; sodium tetrahydroborate; at 20℃;
Preparation of 4-acetamidobenzyl alcohol. To a solution of 4-acetamidobenzaldehyde (10 g, 61.3 mmol) in methanol (100 mE) was added sodium borohydride (800 mg) at room temperature in portions. The reaction mixture was stirred over night, and the progress of reaction checked by TLC using 4:1 hexanes:EtOAc as eluent. Absence of starting material indicated the completion of reduction and the reaction mixture was concentrated in a rotavap. The residue was partitioned between water (25 mE) and ethyl acetate (4x50 mE) and the organic layer was washed with brine (25 mE). The ethyl acetate layer was dried over anhydrous sodium sulfate and the removal of the solvent gave the alcohol as a pale yellow solid, which was dried under high vacuum. 8.6 g (85%); ?H NMR (DMSO-d5): oe 2.0 (s, 3H), 4.5 (d, 2H), 5.2 (t, 1H), 7.25 (d, 2H), 7.55 (d, 2H), 9.95 (s, 1H) ppm.
61%
With ReOBr2(2-(2-hydroxy-5-methylphenyl)benzotriazole-(H))(PPh3); phenylsilane; In tetrahydrofuran; for 1.33333h;Reflux;
General procedure: In a typical experiment, to a mixture of carbonyl compound (1.0mmol) and [ReOBr2(hmpbta)(PPh3)] (5mol%) in THF (3mL) at reflux temperature was added PhSiH3 (2.0mmol). The reaction mixture was stirred under air atmosphere (the reaction times are indicated in the Table 4) and the progress of the reaction was monitored by TLC or 1H NMR. Upon completion, the reaction was quenched with 1equiv of tetrabutylammonium fluoride (TBAF) (1.0M THF) during 1h. Then, the reaction mixture was evaporated and purified by silica gel column chromatography with the appropriate mixture of n-hexane and ethyl acetate to afford the alcohols, which are all known compounds.
Reference Example 24 4-hydroxymethylacetanilide To a solution of methyl 4-acetamidebenzoate (483 mg, 2.5 mmol) in tetrahydrofuran (10 mL) was added under ice-cooling lithium aluminum hydride (190 mg, 5 mmol) and the mixture was stirred at room temperature for 1 h. The reaction mixture was stirred under ice-cooling and 1N hydrochloric acid was added. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an almost pure title compound (230 mg, 56%). 1H-NMR (delta ppm, CDCl3): 2.02 (3H, s), 4.42 (2H, br s), 5.00-5.15 (1H, br), 6.53 (1H, br s), 7.22 (2H, d, J=8.8 Hz), 7.51 (2H, d, J=8.4 Hz)
14
[ 623-04-1 ]
[ 108-24-7 ]
[ 16375-88-5 ]
Yield
Reaction Conditions
Operation in experiment
98%
With Co3O4 nanoparticles; at 20℃; for 0.2h;Green chemistry;
General procedure: In a round-bottomed flask (25 mL) equipped with a magnetic stirrer, a mixture of aniline (0.093 g, 1 mmol) and Co3O4 (0.006 g) was prepared. Acetic anhydride (0.102, 1 mmol) was then added to the reaction mixture and stirring was continued at room temperature for 3 min. The progress of the reaction was followed by TLC. After the reaction completion, the products was extracted with EtOAc and filtered to remove Co3O4. The organic solvent was then washed with H2O (2 x 10 mL) and saturated NaHCO3 solution and then dried over anhydrous Na2SO4. The solvent was removed under vacuum to afford the pure product.
91%
In neat (no solvent); at 20℃; for 0.1h;
General procedure: Alcohol, phenol, and/or amine (1 mmol) were added to amixture of the ZnAl2O4SiO2 nanocomposite (100 mg) andacetic anhydride (1 mmol). The mixture was stirred at 75 C(for alcohols and phenols) or at room temperature (for amines)for a time. The progress of the reaction was monitored by TLCand/or GC-MS. When the reaction was completed, ethyl acetate(10 mL) was added and the mixture was filtered to separate offthe catalyst. The catalyst was washed twice with 7.5 mL ethylacetate. The combined organic phases were washed with a10% solution of NaHCO3 and then dried over MgSO4. The solventwas removed to yield the product. If further purificationwas needed, the product was passed through a short column ofsilica gel. All products were characterized on the basis ofGC-MS, FT-IR, and 1H-NMR spectral data by comparing thesespectra with those of standard samples or literature data.
91%
In water; at 50℃; for 0.15h;
General procedure: In a round-bottom flask (10 mL) equipped with a magnetic stirrer, a mixture of PhNH2(1 mmol, 0.093 g) and H2O(3 mL) in oil bath (50 C) was prepared. Magnetically recyclable nanoparticles of Fe3O4/Cu (0.05 mmol) was then added, and the mixture was stirred for 1 min under oil bath conditions. Addition of Ac2O(1 mmol, 0.102 g) to the prepared mixture was followed by stirring for 3 min at 50 C. After completion of the reaction, the copper nanocatalyst was separated by an external magnet and the mixture was extracted with EtOAc (3 × 8 mL). Organic layers were then dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure affords the pure acetanilide in 95% yield (0.128 g, Table 2, entry 1).
In ethanol; water; at 70℃;
General procedure: In a round-bottom flask (25 mL), a solution of nitrobenzene (0.123 g, 1 mmol) in H2O-EtOH (1.5:0.5 mL) was prepared. Magnetically, nanoparticles of NiFe2O4(at)Cu (0.15 g) were added, and the resulting mixture was stirred for 5 min. Afterward,NaBH4 (0.094 g, 2.5 mmol) was added and the resulting mixture was continued to stirring for 1 min at 70 C. After reduction of nitrobenzene to aniline (monitored by TLC), Ac2O (0.204 g, 2 mmol) was added and the resulting mixture was stirred for 1 min at 70 C. The nanocatalyst was separated by an external magnet, and the mixture was extracted with EtOAc (3 × 5 mL). The organic layer was dried over anhydrous Na2SO4. Evaporation of the solvent affords the pure acetanilide in 95% yield (0.128 g, Table 3,entry 1).
With boron trifluoride diethyl etherate; cesium iodide; In acetonitrile;Product distribution / selectivity;
To a cooled solution of anhyd. DMF (5 mL) was added thionyl chloride (0.2 mL, 2.8 mmol). The mixture was stirred for 10 min and a solution of KI (2.49 g, 15 mmol) in anhyd. DMF (12 mL) was added followed by the addition of alcohol (0.165 g, 1 mmol). The reaction mixture was stirred in the ice-bath for 3 h and allowed to stir at r.t. overnight. The reaction mixture was poured into ice-water (25 mL) and extracted with ether (3×25 mL). The ether layer was washed with brine, dried over anhyd. sodium sulfate and concentrated to remove the solvent. The product was obtained (138 mg, 50%) as a clean yellow solid. (TLC Hex: EtOAc (1:1). 1H NMR (CDCl3): delta 2.17 (s, 3H), 4.45 (s, 2H), 7.17(br. s, 1H), 7.33 (d, 2H), 7.43 (d, 2H). This compound was also prepared with improved yields (75%) using cesium iodide and boron trifluoride etherate in acetonitrile. The coupling of 4-acetamidobenzyl iodide with 3'dApsU2'OMe was done as described for the cholic acid analog before.
50%
To a cooled solution of anhyd. DMF (5 mL) was added thionyl chloride (0.2 mL, 2.8 mmol). The mixture was stirred for 10 min and a solution of KI (2.49 g, 15 mmol) in anhyd. DMF (12 mL) was added followed by the addition of alcohol (0.165 g, 1 mmol). The reaction mixture was stirred in the ice-bath for 3 h and allowed to stir at r.t. overnight. The reaction mixture was poured into ice-water (25 mL) and extracted with ether (3*25 mL). The ether layer was washed with brine, dried over anhyd. sodium sulfate and concentrated to remove the solvent. The product was obtained (138 mg, 50%) as a clean yellow solid. (TLC Hex: EtOAc (1:1). 1H NMR (CDCl3): delta 2.17 (s, 3H), 4.45 (s, 2H), 7.17(br. s, 1H), 7.33 (d, 2H), 7.43 (d, 2H).
50%
With thionyl chloride; potassium iodide; In N,N-dimethyl-formamide; at 20℃;Cooling with ice;
Preparation of 4-acetamidobenzyl iodide. To a cooled solution of anhyd. DMF (5 mE) was added thionyl chloride (0.2 mE, 2.8 mmol). The mixture was stirred for 10 mm andsolution of KI (2.49 g, 15 mmol) in anhyd. DMF (12 mE) was added followed by the addition of the alcohol prepared above (0.165 g, 1 mmol). The reaction mixture was stirred in the ice-bath for 3 h and allowed to stir at r.t. overnight. The reaction mixture was poured into ice-water (25 mE) and extracted with ether (3x25 mE). The ether layer was washed with brine, dried over anhyd. sodium sulfate and concentrated to remove the solvent. The product was obtained (138 mg,50%) as a clean yellow solid. (TEC Hex:EtOAc (1:1). ?H NMR (CDC13): oe 2.17 (s, 3H), 4.45 (s, 2H), 7.17 (bts, 1H), 7.33 (d, 2H), 7.43 (d, 2H) ppm. This compound was also prepared with improved yields (.-45%) using cesium iodide and boron trifluoride etherate in acetonitrile. The coupling of 4-acetamidobenzyl iodide with 3? dApsU2?OMe was done as described for the cholic acid analog before.
A. (4-Acetamido)-phenylmethyl-4-nitrophenylcarbonate. To a solution of 242.8 mg of p-nitrophenyl chloroformate in 5 mL of acetonitrile at 0 C. was added sequentially, 165.2 mg of <strong>[16375-88-5]4-acetamidobenzyl alcohol</strong> and 0.13 mL of 4-methyl morpholine. The mixture was stirred for 24 hours and concentrated in vacuo. The residue was taken up in CH2 Cl2 and washed with 5% sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield 320 mg of the title compound. TLC: Rf=0.23, 50% EtOAc/hexane.
In dichloromethane; acetonitrile;
A. (4-Acetamido)-phenylmethyl-4-nitrophenylcarbonate To a solution of 242.8 mg of p-nitrophenyl chloroformate in 5 mL of acetonitrile at 0 C. was added sequentially, 165.2 mg of <strong>[16375-88-5]4-acetamidobenzyl alcohol</strong> and 0.13 mL of 4-methyl morpholine. The mixture was stirred for 24 hours and concentrated in vacuo. The residue was taken up in CH2 Cl2 and washed with 5% sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield 320 mg of the title compound. TLC: Rf=0.23, 50% EtOAc/hexane.
With triethylamine; In tetrahydrofuran; ethyl acetate;
Reference Example 25 4-chloromethylacetanilide To a solution of 4-hydroxymethylacetanilide (230 mg, 1.4 mmol) in tetrahydrofuran (5 mL) were added under ice-cooling triethylamine (0.39 mL, 2.8 mmol) and methanesulfonyl chloride (0.17 mL, 2 mmol) and the mixture was stirred at roomtemperature for 2 h. The solvent was evaporated under reduced pressure and the obtained residue was dissolved in ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an almost pure title compound (200 mg, 78%). 1H-NMR (delta ppm, CDCl3): 2.18 (3H, s), 4.56 (2H, s), 7.28-7.38 (3H, m), 7.50 (2H, d, J=8.6 Hz)
With 1,4-diaza-bicyclo[2.2.2]octane; TEMPOL; ammonia; copper(l) chloride; In water; acetonitrile; at 20℃; for 24h;
General procedure: To a 25-mL Schlenk tube equipped with a magnetic stirrer, CuCl (0.05 mol, 5 mol%), DABCO (0.10 mol, 10 mol%), 4-HO-TEMPO (0.05 mmol, 5 mol%) were added. Substrates 1 (1 mmol) and NH3 (aq, 25-28%, 3 mmol, 3.0 equiv) in CH3CN (2 mL) were added subsequently. Then the reaction mixture was stirred at room temperature for 24 h in the presence of an air balloon. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4. Subsequently, the combined organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography to afford the corresponding products.
N-(4-(((8-hydroxyquinolin-5-yl)methoxy)methyl)phenyl)acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
General procedure: To a solution of substituted benzyl alcohol 3(6 mmol) in anhydrous THF(30ml) was added sodium hydride (60% dispersion in mineral oil, 0.72g, 18 mmol) at 0 C. The suspension was stirred at 0 C for 30 minutes. Salt 2 (1.15g, 5mmol) was added to the suspension. The mixture was stirred at r.t for 3 hours. Water was added to the suspension, the mixture became homogeneous. The mixture was extracted by ethyl acetate and washed with brine, dried over anhydrous sodium sulfate and concentrated to get the crude. The crude compound was purified by flash chromatography (ethyl acetate: hexane 3:1).
2(S)-(4-acetamidobenzyloxy)-2H-pyran-3(6H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
22%
With tin(IV) chloride; In dichloromethane; at -18℃; for 1h;
A solution of 1 (100 mg, 0.39 mmol) and <strong>[16375-88-5]4-acetamidobenzyl alcohol</strong>(97 mg, 0.58 mmol) in anhydrous CH2Cl2 (4 mL) was cooled at -18 C.Upon addition of SnCl4 (0.06 mL, 0.51 mmol), the reaction mixture wasstirred at -18 C for 1 h and then was diluted with CH2Cl2 and washedwith sat aq NaHCO3, water and brine. After drying (MgSO4) and concentration,the residue was purified by column chromatography(hexane/EtOAc, 7:3?1:1) to afford 27S (22 mg, 22%); [alpha]D -132.8 (c0.8, CHCl3); ee=80%.
With 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate; In acetonitrile; at 20℃; for 5h;Irradiation;
In air, p-aminobenzyl alcohol (0.2 mmol, 27 mg) was dissolved in acetonitrile (2 mL), and then Mes-Acr-MeBF4 (2 mol%, 2 mg) and thioacetic acid (0.4 mmol, 30 mg) were added. The mixture was stirred for 5 hours at room temperature under a 36W blue LED. The mixture was quenched with water (2 mL) and then extracted with EtOAc (3 x 4 mL). The organic phase was washed with brine, dried over Na 2 SO 4 and spin-dried, and then separated by column chromatography to obtain 26 mg of a white solid product with a yield of 79%.
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