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Structure of 4412-91-3 * Storage: {[proInfo.prStorage]}
* 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.
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 0.75 h;
To a solution of ethyl 3-furoate (7) (4.00 g, 28.5 mmol) in Et2O (140 mL) was added LiAlH4 (1.62 g, 42.8 mmol) in small portions at 0 °C. The reaction mixture was stirred at room temperature for 45 min, followed by quenching with H2O (2 mL), NaOH 1M (2 mL) and H2O (6 mL) at 0 °C. The resulting white precipitate was filtered off and the solvent was removed under reduced pressure affording compound 8 (2.60 g, 93percent) as a yellowish oil. Rf=0.2 (hexane/ethyl acetate, 4:1). 1H NMR (CDCl3): δ=7.42–7.41 (m, 1H, H2), 7.40–7.39 (m, 1H, H5), 6.44–6.42 (m, 1H, H4), 4.55 (s, 2H, CH2), 1.81 (br s, 1H, OH). 13C NMR (CDCl3): δ=143.3 (C5), 139.9 (C2), 125.1 (C3), 109.9 (C4), 56.1 (CH2). HRMS-EI: m/z [M]+ calcd for C5H6O2: 98.0368, found: 98.0371.
Reference：
[1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 9, p. 2661 - 2679
[2] European Journal of Medicinal Chemistry, 2015, vol. 94, p. 113 - 122
[3] Tetrahedron Letters, 1982, vol. 23, # 31, p. 3115 - 3118
[4] Tetrahedron Asymmetry, 2014, vol. 25, # 8, p. 677 - 689
[5] Journal of Medicinal Chemistry, 1998, vol. 41, # 4, p. 602 - 617
2
[ 498-60-2 ]
[ 4412-91-3 ]
Yield
Reaction Conditions
Operation in experiment
99%
With sodium tetrahydroborate; water In diethyl ether at 0 - 20℃; for 0.5 h;
0°C , water (15mL) added 3 aldehyde 4 (14.1g, purity 97percent, 147mmol) in ether (150mL) solution, with vigorous stirring added Sodium borohydride (8.94g, 235mmol), the addition was completed, brought to room temperature stirring was continued for 0.5h, the raw material disappeared; adding water, the upper ether layer was separated, the aqueous layer was extracted three times with ether, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed distillation diethyl ether; the remaining liquid was distilled under reduced pressure to give a colorless liquid 5 (13.96g, 99percent).
93.2%
With hydrogen In isopropyl alcohol at 110℃; for 3 h; Autoclave
General procedure: FFR (99percent, Sigma-Aldrich) 1 mL and various amounts of thenickel catalysts were added to 30 mL of a solvent (methanol(99.8percent, Duksan), ethanol, IPA, or methyl isobutyl ketone (MIBK;99.5percent, TCI)). Raney Ni (Ni 92.5percent, TCI) was washed with ethanoland distilled water twice each and dried in a vacuum oven at50 °C before use. The mixed solution was placed in a 100 mL Teflonliner with a magnetic stir-bar and sealed in a stainless steel autoclave.Then the reactor was purged with H2 three times to excludeother gases. The autoclave was heated to 110 °C at which temperaturethe hydrogenation reaction was performed under 30 bar H2and stirring at 700 rpm. After the reaction, the autoclave wascooled, and the solution was subsequently centrifuged at11,000 rpm for 10 min to separate the liquid-phase products fromthe catalyst. For the recycling tests, 1 mL of FFR and 30 mL of IPAwere added to the centrifuged Ni catalyst without any furthertreatment. The products were analyzed by a gas chromatograph(GC; YL 6100) equipped with a capillary column (DB-624, AgilentTechnologies, 30 m 0.53 mm 3.00 lm) and flame ionizationdetector (FID).The selective hydrogenation of various unsaturated aldehydesand ketones was performed according to the following protocol.The reactant 1 mL (3-cyclohexene-1-carboxaldehyde (97percent,Sigma-Aldrich), 5-hydroxymethyl-2-furaldehyde (99percent, Sigma-Aldrich), 5-methylfurfural (99percent, Sigma-Aldrich), 2-thiophenecarboxaldehyde (98percent, Sigma-Aldrich), pyrrole-2-carboxaldehyde (98percent, Sigma-Aldrich), 3-furancarboxaldehyde(P97percent, Sigma-Aldrich), 2-furyl methyl ketone (99percent, Sigma-Aldrich), acetophenone (99percent, Sigma-Aldrich), cinnamaldehyde(99percent, Sigma-Aldrich), or trans-2-hexen-1-al (98percent, Sigma-Aldrich))was added to 30 mL of IPA. The 6.8 nm Ni nanoparticle catalyst(20 mg) was charged to the reactor. The hydrogenation reactionswere then performed according to the FFR hydrogenation protocol,except the reaction temperature was 100 °C for 3-cyclohexene-1-carboxaldehyde.
92%
With sodium tetrahydroborate; sodium hydroxide In methanol; water for 0.5 h;
General procedure: Preparation of 1,2-di(fur-3-yl) was carried out via procedures similar to those used for the preparation of 1n, and all of the experimental procedures are summarized as follows: Reduction of furan-3-carboxaldehyde: 0.02 mol of furan-3-carboxaldehyde was used as the starting material to synthesize (fur-3-yl)-methanol (92percent yield). Chlorination of (fur-3-yl)methanol: 0.01 mol of (fur-3-yl)methanol was used as the starting material to synthesize (fur-3-yl)methyl chloride, without characterization. Wittig Reaction: 24 mmol of triphenylphosphine and 20 mmol of (fur-3-yl)methyl chloride were used to synthesize triphenylphosphonium salt. Then, 10 mmol of the triphenylphosphonium salt, 11 mmol of 3-fural, and all of the other necessary reagents were used to synthesize cis- and trans-1,2-di(fur-3-yl)ethene 1p, obtaining a total yield 32percent. The cis and trans forms were purified via silica gel chromatography using hexane for characterization.
Reference：
[1] Chemistry - An Asian Journal, 2015, vol. 10, # 4, p. 976 - 981
[2] Patent: CN103408559, 2016, B, . Location in patent: Paragraph 0066-0068
[3] Combinatorial Chemistry and High Throughput Screening, 2012, vol. 15, # 1, p. 81 - 89
[4] Journal of Catalysis, 2016, vol. 344, p. 609 - 615
[5] Tetrahedron, 2014, vol. 70, # 9, p. 1748 - 1762
[6] Organic Letters, 2007, vol. 9, # 26, p. 5429 - 5432
[7] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 9, p. 3100 - 3110
[8] Journal of Organic Chemistry, 2007, vol. 72, # 2, p. 538 - 549
[9] Chemistry - A European Journal, 2006, vol. 12, # 10, p. 2739 - 2744
[10] Chemistry - A European Journal, 2013, vol. 19, # 24, p. 7701 - 7707
[11] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5781 - 5788
3
[ 614-98-2 ]
[ 4412-91-3 ]
[ 30614-67-6 ]
Yield
Reaction Conditions
Operation in experiment
65%
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 0.75 h; Inert atmosphere
A suspension of LiAlH4 (516 mg, 13 mmol) in dry diethyl ether (10 mL) was placed in an oven-dried two-necked flask, fitted with a condenser, magnetic stirring and nitrogen atmosphere. Then, a solution of ethyl 3-furoate (2 g, 13.6 mmol) in dry diethyl ether (10 mL) was added, at room temperature. Immediately, generation of H2 was observed. The reaction mixture was kept under these conditions for 45 min (control by gas chromatography). The excess of hydride was quenched by adding ethyl acetate (50 mL). Then, the reaction mixture was washed with water (5×20 mL). The aqueous phase was extracted with ethyl acetate (2×20 mL) and all organic phases were combined together, dried with anhydrous MgSO4, and concentrated to dryness. The residue was submitted to a flash column chromatography (SiO2, eluting it with mixtures of hexane and ethyl acetate of increasing polarity) obtaining, with hexane/ethyl acetate (8:2), 3-furylmethanol (850 mg, yield=65percent) as a transparent oil. The resulting product was very volatile, so, the process of concentration in the rotary evaporator must be carried out at 0 °C or by simple distillation. IR (film, ν, cm−1): 3350 (H–O, st), 3080, 2980, 1610, 1520, 1460, 1400, 1160, 1030, 970, 880. 1H NMR (200 MHz, CDCl3, δ, ppm): 4.55 (2H, s, H1), 6.43 (1H, dd, J1=1.8 Hz, J2=0.8 Hz, H4′), 7.40 (2H, dd, J1=1.8 Hz, J2=0.8 Hz, H2′ and H5′). 13C NMR (50 MHz, CDCl3, δ, ppm): 56.6 (C1), 109.7 (C4′), 125.0 (C3′), 139.8 (C2′), 143.3 (C5′). MS [GC–MS (CI), NH3, 70 eV, 150 °C, m/z, (percent)]: 132 (100, M+N2H6), 115 (14, M+NH3), 98 (13, M+). GC (50 °C, 1 min, 10 °C/min, 250 °C, 15 min): tR=5.6 min. TLC (SiO2, hexane/ethyl acetate, 1:1): Rf=0.55 (black color, developed with anisaldehyde–H2SO4 reagent). EA. Calculated for C5H6O3: C (61.22percent), H (6.16percent). Found: C (61.19percent), H (6.20percent).
Reference：
[1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1989, vol. 38, # 1.2, p. 131 - 134[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1989, vol. 38, # 1, p. 144 - 147
[3] Journal of the American Chemical Society, 2017, vol. 139, # 26, p. 8788 - 8791
[4] Tetrahedron Letters, 1994, vol. 35, # 40, p. 7401 - 7404
[5] Tetrahedron, 1996, vol. 52, # 37, p. 12137 - 12158
[6] Chemical Communications, 2004, # 1, p. 44 - 45
[7] Journal of the American Chemical Society, 1981, vol. 103, # 11, p. 3112 - 3120
[8] Organic and Biomolecular Chemistry, 2006, vol. 4, # 6, p. 1020 - 1031
[9] Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8741 - 8749
[10] Journal of the American Chemical Society, 1950, vol. 72, p. 2195,2198
[11] Australian Journal of Chemistry, 1989, vol. 42, # 12, p. 2181 - 2190
[12] Acta chemica Scandinavica (Copenhagen, Denmark : 1989), 1989, vol. 43, # 4, p. 381 - 385
[13] Tetrahedron Asymmetry, 2014, vol. 25, # 8, p. 677 - 689
5
[ 101822-35-9 ]
[ 4412-91-3 ]
Reference：
[1] Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8741 - 8749
[2] Tetrahedron Letters, 1989, vol. 30, # 14, p. 1765 - 1768
6
[ 117657-69-9 ]
[ 4412-91-3 ]
Reference：
[1] Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8741 - 8749
[2] Tetrahedron Letters, 1989, vol. 30, # 14, p. 1765 - 1768
7
[ 117657-62-2 ]
[ 4412-91-3 ]
Reference：
[1] Tetrahedron Letters, 1987, vol. 28, # 48, p. 5965 - 5968
[2] Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8741 - 8749
8
[ 117657-58-6 ]
[ 4412-91-3 ]
[ 117657-73-5 ]
[ 117657-69-9 ]
Reference：
[1] Tetrahedron Letters, 1987, vol. 28, # 48, p. 5965 - 5968
[2] Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8741 - 8749
9
[ 88-14-2 ]
[ 4412-91-3 ]
Reference：
[1] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 2925 - 2933
With lithium aluminium hydride In diethyl ether 1) 10 deg C, 30 min, 2) 25 deg C, 1 h;
93%
With lithium aluminium hydride In diethyl ether at 0 - 20℃; for 1h; Schlenk technique; Inert atmosphere;
91%
With lithium aluminium hydride In diethyl ether
91%
With lithium aluminium hydride In diethyl ether for 2h;
85%
With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 12h;
83%
With lithium aluminium hydride In tetrahydrofuran for 22h; Heating;
80%
With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 24h;
77%
With lithium aluminium hydride In diethyl ether for 6h; Ambient temperature;
63.1%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 1h;
69.69A Example 69A: furan-3-ylmethanol
To a solution of furan-3-carboxylic acid (50 g, 446 mmol) in tetrahydrofuran(500 mL) was added a solution of borane in tetrahydrofuran (669 mL, 669 mmol) at 0 °C, and the mixture was stirred at 20 °C for 1 hour. One additional vial on 25 g scale and six additional vials on 50 g scale were set up as described above. The reactions conducted in parallel were combined for work up. After cooling to 0 °C, the reaction mixture was quenched with water until gas evolution had ceased. After bulk solvent removal, the resulting crude residue was then partitioned between saturated aqueous NaHCO3 and ethyl acetate, and the aqueous layer was further extracted with ethyl acetate (2 × 1000 mL). The combined organic phases were washed with brine (1000 mL), dried Na2SO4, and concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel with petroleum ether: ethyl acetate= 3:1 to give the title compound (230 g, yield 63.1%) as a yellow oil.1HNMR (400 MHz,DMSO-d6) ppm 7.46 - 7.61 (m, 2 H), 4.34 (d, J=5.50 Hz, 2 H), 4.97 (t, J=5.50 Hz, 1 H), 6.44(d, J=0.63 Hz, 1 H).
63.1%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 1h;
69A Example 69A: furan-3-ylmethanol
To a solution of furan-3-carboxylic acid (50 g, 446 mmol) in tetrahydrofuran(500 mL) was added a solution of borane in tetrahydrofuran (669 mL, 669 mmol) at 0 °C, and the mixture was stirred at 20 °C for 1 hour. One additional vial on 25 g scale and six additional vials on 50 g scale were set up as described above. The reactions conducted in parallel were combined for work up. After cooling to 0 °C, the reaction mixture was quenched with water until gas evolution had ceased. After bulk solvent removal, the resulting crude residue was then partitioned between saturated aqueous NaHCO3 and ethyl acetate, and the aqueous layer was further extracted with ethyl acetate (2 × 1000 mL). The combined organic phases were washed with brine (1000 mL), dried Na2SO4, and concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel with petroleum ether: ethyl acetate= 3:1 to give the title compound (230 g, yield 63.1%) as a yellow oil. 1HNMR (400 MHz, DMSO-d6) δ ppm 7.46 - 7.61 (m, 2 H), 4.34 (d, J=5.50 Hz, 2 H), 4.97 (t, J=5.50 Hz, 1 H), 6.44 (d, J=0.63 Hz, 1 H).
59%
With lithium aluminium hydride In diethyl ether at 0 - 20℃; for 2h;
55.7%
With borane-THF In tetrahydrofuran at 20℃; for 2h;
27.1 Step 1: Synthesis of furan-3-ylmethanol
The furan-3-carboxylic acid (25 g, 0.22 mmol, 1.0 eq) was dissolved in tetrahydrofuran (330 mL).A borane-tetrafuran solution (1 mol/L, 330 mL) was slowly added dropwise under ice-cooling, and the mixture was stirred at room temperature for 2 hours. TLC showed the reaction was completed, and methanol (40 mL) was slowly added dropwise in an ice bath to quench the reaction. Concentrated under reduced pressure, ethyl acetate (500 mL) was evaporated and evaporated.The crude product was purified by silica gel column chromatography (ethyl ether: ethyl acetate=4:1 v/v)Product (12 g, yield: 55.7%).
With lithium aluminium hydride; diethyl ether
6.8 g
With lithium aluminium hydride In diethyl ether for 6h; Heating;
270.A Example 270A: furan-3-ylmethanol
To a solution of furan-3-carboxylic acid (50 g, 446 mmol) in tetrahydrofuran(500 mL) was added a 1 N solution of borane in tetrahydrofuran (669 mL, 669 mmol) at 0 °C, and the mixture was stirred at 20 °C for 1 hour. One additional vial on 25 g scale and six additional vials on 50 g scale were set up as described above. The reactions conducted in parallel were combined for work up. After cooling to 0 °C, the reaction mixture was quenched with water until gas evolution had ceased. After bulk solvent removal, the resulting crude residue was then partitioned between saturated aqueous NaHCO3 and ethyl acetate, and the aqueous layer was further extracted with ethyl acetate (2 1000 mL). The combined organic phases were washed with brine (1000 mL), dried Na2SO4, and concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel with petroleum ether: ethyl acetate= 3:1 to give the title compound (230 g, yield 63.1%). 1HNMR (400 MHz, DMSO-d6) d ppm 7.46 - 7.61 (m, 2 H), 4.34 (d, J=5.50 Hz, 2 H), 4.97 (t, J=5.50 Hz, 1H), 6.44 (d, J=0.63 Hz, 1H).
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h;
93%
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 0.75h;
4.1.1 3-Furylmethanol (8)
To a solution of ethyl 3-furoate (7) (4.00 g, 28.5 mmol) in Et2O (140 mL) was added LiAlH4 (1.62 g, 42.8 mmol) in small portions at 0 °C. The reaction mixture was stirred at room temperature for 45 min, followed by quenching with H2O (2 mL), NaOH 1M (2 mL) and H2O (6 mL) at 0 °C. The resulting white precipitate was filtered off and the solvent was removed under reduced pressure affording compound 8 (2.60 g, 93%) as a yellowish oil. Rf=0.2 (hexane/ethyl acetate, 4:1). 1H NMR (CDCl3): δ=7.42-7.41 (m, 1H, H2), 7.40-7.39 (m, 1H, H5), 6.44-6.42 (m, 1H, H4), 4.55 (s, 2H, CH2), 1.81 (br s, 1H, OH). 13C NMR (CDCl3): δ=143.3 (C5), 139.9 (C2), 125.1 (C3), 109.9 (C4), 56.1 (CH2). HRMS-EI: m/z [M]+ calcd for C5H6O2: 98.0368, found: 98.0371.
91%
With lithium aluminium tetrahydride
72%
With lithium aluminium tetrahydride In diethyl ether at 20℃; Inert atmosphere;
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃;
EXAMPLE 15 5-Chloro-1-(3-furylmethyl)pyrimidin-2-one N,N-Dimethylformamide dineopentyl acetal (1.8 ml) was added to a stirred mixture of <strong>[54326-16-8]5-chloropyrimidin-2-one</strong> (522 mg) and 3-furanmethanol (0.48 ml) in dry N,N-dimethylformamide (10 ml) under nitrogen and the mixture was then heated at 90 C. After 11/4 h the reaction mixture was evaporated to dryness and then the residue was dissolved in ethyl acetate (200 ml) and the solution washed with water (3*50 ml), dried (MgSO4) and concentrated to ca 15 ml by which time crystallisation had occurred. The suspension was cooled and then the crystals collected and recrystallized from ethyl acetate to give white crystals of the title pyrimidinone (288 mg), m.p. 161.5-162 C., lambdamax (EtOH) 333 nm (epsilon 2,340), lambdainf 245 nm (epsilon 4,000).
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 0.75h; Inert atmosphere;
4.4.6 Synthesis of 3-furylmethanol, 12
A suspension of LiAlH4 (516 mg, 13 mmol) in dry diethyl ether (10 mL) was placed in an oven-dried two-necked flask, fitted with a condenser, magnetic stirring and nitrogen atmosphere. Then, a solution of ethyl 3-furoate (2 g, 13.6 mmol) in dry diethyl ether (10 mL) was added, at room temperature. Immediately, generation of H2 was observed. The reaction mixture was kept under these conditions for 45 min (control by gas chromatography). The excess of hydride was quenched by adding ethyl acetate (50 mL). Then, the reaction mixture was washed with water (5×20 mL). The aqueous phase was extracted with ethyl acetate (2×20 mL) and all organic phases were combined together, dried with anhydrous MgSO4, and concentrated to dryness. The residue was submitted to a flash column chromatography (SiO2, eluting it with mixtures of hexane and ethyl acetate of increasing polarity) obtaining, with hexane/ethyl acetate (8:2), 3-furylmethanol (850 mg, yield=65%) as a transparent oil. The resulting product was very volatile, so, the process of concentration in the rotary evaporator must be carried out at 0 °C or by simple distillation. IR (film, ν, cm-1): 3350 (H-O, st), 3080, 2980, 1610, 1520, 1460, 1400, 1160, 1030, 970, 880. 1H NMR (200 MHz, CDCl3, δ, ppm): 4.55 (2H, s, H1), 6.43 (1H, dd, J1=1.8 Hz, J2=0.8 Hz, H4′), 7.40 (2H, dd, J1=1.8 Hz, J2=0.8 Hz, H2′ and H5′). 13C NMR (50 MHz, CDCl3, δ, ppm): 56.6 (C1), 109.7 (C4′), 125.0 (C3′), 139.8 (C2′), 143.3 (C5′). MS [GC-MS (CI), NH3, 70 eV, 150 °C, m/z, (%)]: 132 (100, M+N2H6), 115 (14, M+NH3), 98 (13, M+). GC (50 °C, 1 min, 10 °C/min, 250 °C, 15 min): tR=5.6 min. TLC (SiO2, hexane/ethyl acetate, 1:1): Rf=0.55 (black color, developed with anisaldehyde-H2SO4 reagent). EA. Calculated for C5H6O3: C (61.22%), H (6.16%). Found: C (61.19%), H (6.20%).
Multi-step reaction with 3 steps
1.1: triethylamine; dmap / tetrahydrofuran / 15 h / 80 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 4 h / -30 °C / Inert atmosphere
2.2: 4 h / -30 - 20 °C / Inert atmosphere
3.1: formic acid / tetrahydrofuran; water / 2 h / 50 °C
Multi-step reaction with 3 steps
1.1: triethylamine; dmap / tetrahydrofuran / 15 h / 80 °C
2.1: trichlorophosphate / 0.5 h / 5 °C / Inert atmosphere
2.2: 4 h / 80 °C / Inert atmosphere
3.1: formic acid / tetrahydrofuran; water / 2 h / 50 °C
With aluminum (III) chloride; triethylamine In dichloromethane at 20℃; for 48h;
General experimental methods for AlCl3-catalyzedCannizzaro/Tishchenko reactions
General procedure: A mixture of AlCl3(0.5 mmol), the aldehyde (10 mmol),and triethylamine (5 mmol) was added to 2 cm3of driedCH2Cl2and stirred for 2 days at room temperature underargon atmosphere until the aldehyde was completelyconsumed. The reaction progress was probed by TLCand GC/MS (Agilent 6890 (GC)/5972A (MS)). The reactionmixture was then filtered through Whatman filterpaper (grade 2), and treated with sodium bicarbonatesolution, followed by isolating the organic phase via aseparatory funnel. The aqueous phase washed severaltimes with CH2Cl2to make sure that all organic materialsextracted. Then, the organic phase was dried usingsodium sulfate and subsequently analyzed by GC/MSand 1H NMR, and validated using melting or boilingpoint of the product.
With aluminum (III) chloride; triethylamine In dichloromethane at 20℃; for 48h;
General experimental methods for AlCl3-catalyzedCannizzaro/Tishchenko reactions
General procedure: A mixture of AlCl3(0.5 mmol), the aldehyde (10 mmol),and triethylamine (5 mmol) was added to 2 cm3of driedCH2Cl2and stirred for 2 days at room temperature underargon atmosphere until the aldehyde was completelyconsumed. The reaction progress was probed by TLCand GC/MS (Agilent 6890 (GC)/5972A (MS)). The reactionmixture was then filtered through Whatman filterpaper (grade 2), and treated with sodium bicarbonatesolution, followed by isolating the organic phase via aseparatory funnel. The aqueous phase washed severaltimes with CH2Cl2to make sure that all organic materialsextracted. Then, the organic phase was dried usingsodium sulfate and subsequently analyzed by GC/MSand 1H NMR, and validated using melting or boilingpoint of the product.
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