* 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] Organic Letters, 2004, vol. 6, # 12, p. 2019 - 2022
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 8, p. 2123 - 2125
[3] Journal of Organic Chemistry, 1996, vol. 61, # 11, p. 3623 - 3634
[4] European Journal of Medicinal Chemistry, 2010, vol. 45, # 2, p. 639 - 646
2
[ 123-08-0 ]
[ 96-32-2 ]
[ 73620-18-5 ]
Yield
Reaction Conditions
Operation in experiment
82%
With potassium carbonate In acetone at 20℃; for 3.5 h;
Methyl 2-(4-formylphenoxy)acetate. To a solution of 4-hydroxybenzaldehyde (3.0 g, 25 mmol) in acetone (61.4 mL), K2C03 (5.43 g, 39.3 mmol) was added and the mixture was stilTed vigorously. Methyibromoacetate (2.8 mL, 29 mmol) was added and the mixture was stirred for 3.5 hrs at room temperature. The reaction mixture was concentrated down under reduced pressure then washed with 11O and extracted with EtOAc. The organic layer was separated, dried over Na2SO4, filtered, and concentrated to give a colorless oil that solidified under vacuum in 82 percent isolated yield. ‘H NMR (400 MHz, CDC13) 3 9.87 (s, 111),7.82 (d, J = 8.8 Hz, 211), 6.98 (d, J = 8.7 Hz, 211), 4.70 (s, 211), 3.79 (s, 3H). ESI-MS (mlz):195.1 [M+Hjt
82%
With potassium carbonate In acetone at 20℃; for 3.5 h;
To a solution of 4-hydroxybenzaldehyde (3.0 g, 25 mmol) in acetone (61.4 mL), K2CO3 (5.43 g, 39.3 mmol) was added and the mixture was stirred vigorously. Methylbromoacetate (2.8 mL, 29 mmol) was added and the mixture was stirred for 3.5 hrs at room temperature. The reaction mixture was concentrated down under reduced pressure then washed with 0 and extracted with EtOAc. The organic layer was separated, dried over Na2S04, filtered, and concentrated to give a colorless oil that solidified under vacuum in 82 percent isolated yield. H NMR (400 MHz, CDC13) δ 9.87 (s, 1H),
82%
With potassium carbonate In acetone at 20℃; for 3.5 h;
To a solution of 4-hydroxybenzaldehyde (3.0 g, 25 mmol) in acetone (61.4 mL), K2CO3 (5.43 g, 39.3 mmol) was added and the mixture was stirred vigorously. Methylbromoacetate (2.8 mL, 29 mmol) was added and the mixture was stirred for 3.5 hrs at room temperature. The reaction mixture was concentrated down under reduced pressure then washed with H2O and extracted with EtOAc. The organic layer was separated, dried over Na2SO4, filtered, and concentrated to give a colorless oil that solidified under vacuum in 82 percent isolated yield. 1H NMR (400 MHz, CDCl3) δ 9.87 (s, 1H), 7.82 (d, J = 8.8 Hz, 2H), 6.98 (d, J = 8.7 Hz, 2H), 4.70 (s, 2H), 3.79 (s, 3H). ESI-MS (m/z): 195.1 [M+H]+.
Reference：
[1] Organic Letters, 2011, vol. 13, # 20, p. 5656 - 5659
[2] Organic Letters, 2004, vol. 6, # 12, p. 2019 - 2022
[3] Chemistry - A European Journal, 2008, vol. 14, # 19, p. 5812 - 5819
[4] Patent: WO2015/65716, 2015, A1, . Location in patent: Paragraph 00490
[5] Patent: WO2016/144958, 2016, A1, . Location in patent: Paragraph 00296
[6] Patent: WO2018/17582, 2018, A1, . Location in patent: Paragraph 00285
[7] Journal of Chemical Research, Miniprint, 1987, # 12, p. 3144 - 3177
[8] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 19, p. 2589 - 2592
[9] Journal of Organic Chemistry, 1996, vol. 61, # 11, p. 3623 - 3634
[10] Patent: US6469167, 2002, B1,
[11] Patent: WO2005/11685, 2005, A1, . Location in patent: Page/Page column 43-44
[12] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 9, p. 2601 - 2605
[13] CrystEngComm, 2010, vol. 12, # 12, p. 4095 - 4100
[14] Organic Process Research and Development, 2012, vol. 16, # 4, p. 586 - 594
[15] Patent: CN103739540, 2016, B, . Location in patent: Paragraph 0100-0103
[16] Chemistry - A European Journal, 2018, vol. 24, # 49, p. 12950 - 12960
3
[ 123-08-0 ]
[ 96-34-4 ]
[ 73620-18-5 ]
Yield
Reaction Conditions
Operation in experiment
66.1%
With potassium carbonate; sodium iodide In acetone for 12 h; Heating / reflux
Example 68 (4-Formylphenoxy)acetic Acid Methyl Ester (68) To a mixture of 4-hydroxy benzaldehyde (200 grams, 1.64 mol), anhydrous K2CO3 (600 grams, 4.34 mol) and sodium iodide (20 grams, 133 mol) in anhydrous acetone (2500 mL) was added methyl chloro acetate (223 grams, 2.055 mol) and refluxed for 12 hours. Acetone was distilled and water (1800 mL) was added. Crude 68 was extracted in to chloroform, dried over Na2SO4, distilled and purified by column chromatography on silica gel using hexane as eluant to give pure 68 (210 grams, 66.1percent) as a white powder.
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 8, p. 2123 - 2125
[2] Patent: US2009/170927, 2009, A1, . Location in patent: Page/Page column 28
[3] Patent: US6469167, 2002, B1,
[4] European Journal of Medicinal Chemistry, 2010, vol. 45, # 2, p. 639 - 646
[5] Steroids, 2012, vol. 77, # 5, p. 552 - 557
[6] Bioorganic Chemistry, 2016, vol. 65, p. 26 - 37
With triphenylphosphine In tetrahydrofuran; diethylazodicarboxylate
EXAMPLE 44 Methyl 2-(4-formylphenoxy)ethanoate A solution of 4-hydroxy benzaldehyde, (1.22 g, 0.01 m), methyl glycolate (0.97 g, 0.01 m), and triphenylphosphine, (3.93 g, 0.015 m), in dry tetrahydrofuran, (50 ml) was stirred with cooling in ice and diethylazodicarboxylate, (2.61 g, 0.015 m), added dropwise. The solution was stirred at room temperature for 0.5 hours, then evaporated in vacuo to dryness. Column chromatography of the residue on silica gel eluding with chloroform yielded 1.30 g (67percent) of the title compound as an oil which crystallized on standing, mp 39°-41° C., νmax (mull) 1750, 1680, 1595, 1575, 1505 cm-1.
6-amino-5-[{4-(2-methoxy-2-oxoethoxy)benzylidene}amino]-1,3-dimethyluracil[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
65%
With acetic acid In methanol at 20℃;
1 General method for the synthesis of various benzylidenederivatives
General procedure: To a stirred solution of 5,6-diamino-1,3-dimethyluracil (4)(1.0 g, 5.87 mmol) in MeOH-AcOH (4:1, 40 ml) was slowly added the solution of above obtained oily residues of requisite substituted aldehydes 5-8 in methanol (24 ml). Yellow colored precipitate appeared during addition. The reaction mixture was further stirred overnight at room temperature and the completion of reaction was monitored by thin layer chromatography. The precipitate obtained was filtered off, washed with methanol and dried to obtain corresponding benzylidene derivatives 9-12.
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