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Chemical Structure| 2011-06-5 Chemical Structure| 2011-06-5

Structure of 2011-06-5

Chemical Structure| 2011-06-5

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Product Details of [ 2011-06-5 ]

CAS No. :2011-06-5
Formula : C15H14O3
M.W : 242.27
SMILES Code : O=CC1=CC=CC(OC)=C1OCC2=CC=CC=C2
English Name :2-(Benzyloxy)-3-methoxybenzaldehyde
MDL No. :MFCD00202674

Safety of [ 2011-06-5 ]

Application In Synthesis of [ 2011-06-5 ]

* 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.

  • Downstream synthetic route of [ 2011-06-5 ]

[ 2011-06-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 2011-06-5 ]
  • [ 89524-98-1 ]
  • [ 2416603-96-6 ]
YieldReaction ConditionsOperation in experiment
94.4% With tetramethylguanidine In tetrahydrofuran at 0 - 5℃; for 1.66667h; Large scale; 1.2 2. Procedure for the preparation of compound 33d To a stirred solution of phosphonate 3k (61 .3 kg. 206 Mci) and tetrarnethylguanidine(248 kg 215 Mol) in 100 kg of THF a solution ol compound 3Th 43 45 kg 179 Mol) in100 kg of THF was added a a temperature beeween o u s °c over a perod of 100 minutes.After the complete addition of reactants. TLC showed complete consumption of compound33b. The TI-IF was removed under reduced pressure and ethyl acetate (129 kg) was addedto the remaining oily mixture. The ethyl acetate phase was washed with it) % citric acidi 14 L) and ith 10 % brine (4 x 39 L) The pui iflcation was pcrfoj mcd u sing silica colunm chromatography with 140 kg silica. The product was eluted with ethyl acetate:hexane (1:4 w/w). The solvents were evaporated under reduced pressure to yield about 70 kg (94.4%) of compound 33d. TLC showed a purity of >99%.
  • 2
  • [ 2011-06-5 ]
  • [ 89524-98-1 ]
  • [ 1644445-37-3 ]
YieldReaction ConditionsOperation in experiment
80% With N,N,N',N'-tetramethylguanidine In tetrahydrofuran at 0 - 20℃; 14.1 Methyl (Z)-3-(2-(Benzyloxy)-3-methoxyphenyl)-2-((tert-butoxycarbonyl)amino)acrylate (+-)-BOC-A-phosphonoglycine trimethyl ester 14b (9.8 g, 33 mmol) and tetramethylguanidine (4.0 g, 34.4 mmol) were dissolved in 100 mL tetrahydrofuran, and the mixture was cooled to 0° C. A solution of 2-(benzyloxy)-3-methoxybenzaldehyde 14a (7.0 g, 28.7 mmol) in tetrahydrofuran (5 mL) was added, and the resulting mixture was reacted overnight at room temperature. After the reaction was completed, the resulting solution was concentrated under reduced pressure, and ethyl acetate (40 mL) was added to dissolve the residue. The resulting mixture was washed with 10% citric acid solution (30 mL) and saturated brine (30 mL) in sequence, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: system A) to obtain methyl (Z)-3-(2-(benzyloxy)-3-methoxyphenyl)-2-((tert-butoxycarbonyl) amino)acrylate 14c (9.5 g, white solid), yield: 80%. MS m/z(ESI): 314.0 [M-100]
80% With N,N,N',N'-tetramethylguanidine In tetrahydrofuran at 0 - 20℃; 1 (Z)-Methyl 3-(2-(benzyloxy)-3-methoxyphenyl)-2-((tert-butoxycarbonyl)amino)acrylate (±)-BOC-A-phosphonoglycine trimethyl ester 1b (9.8 g, 33 mmol) and tetramethylguanidine (4.0 g, 34.4 mmol) were dissolved in 100 mL of tetrahydrofuran, and the reaction solution was lowered to 0 °C,A tetrahydrofuran solution (5 mL) of 2-(benzyloxy)-3-methoxybenzaldehyde 1a (7.0 g, 28.7 mmol) was added, and the reaction was carried out at room temperature overnight. After the reaction was completed, it was concentrated under reduced pressure, ethyl acetate (40 mL) was added to dissolve the residue, washed with 10% citric acid solution (30 mL) and saturated brine (30 mL) successively, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure , the obtained residue was purified by silica gel column chromatography (eluent: A system),(Z)-methyl 3-(2-(benzyloxy)-3-methoxyphenyl)-2-((tert-butoxycarbonyl)amino)acrylate 1c (9.5 g, white solid) was obtained as Rate: 80%
 

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