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Structure of 3775-29-9

Chemical Structure| 3775-29-9

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Product Details of [ 3775-29-9 ]

CAS No. :3775-29-9
Formula : C8H12O4
M.W : 172.18
SMILES Code : C=C(COC(C)=O)COC(C)=O
MDL No. :MFCD00797462
InChI Key :FKAKGSJLTBVQOP-UHFFFAOYSA-N
Pubchem ID :77404

Safety of [ 3775-29-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 3775-29-9 ]

* 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 [ 3775-29-9 ]

[ 3775-29-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 3775-29-9 ]
  • [ 120686-00-2 ]
  • [ 179105-08-9 ]
  • 2
  • [ 3775-29-9 ]
  • [ 120686-00-2 ]
  • (+/-)-7,8,9,10-Tetrahydro-2-methoxy-7-methylene-11-oxo-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylic acid methyl ester [ No CAS ]
  • 3
  • [ 3775-29-9 ]
  • [ 3513-81-3 ]
YieldReaction ConditionsOperation in experiment
98% With pyridine; dmap; In dichloromethane; at 0 - 20℃; for 0.5h; General procedure: Allyl alcohol (1 equiv.) and acetic anhydride (1.2 equiv.) were dissolved in DCM (-1M) at 0°C. Pyridine (1 equiv.) and DMAP (0.1 molpercent) were then added. The reaction mixture was stirred at 0 °C for 30 mm. and was then allowed to reach room temperature. After completion, the mixture was quenched with 2N HCI and the organic layer was washed with H20, brine and was dried over Na2SO4. Careful evaporation of the remaining solvents affords the pure compound without further purification.; 2-methylenepropane-1,3-diyl diacetate (2d). Prepared by general procedure B with the following notes:Column chromatography (hexanes ? ethyl acetate 20:1) affords the titled compound as a colorless oil (20g , 91 percent). Analytical data are identical to those in the reference.14
  • 5
  • [ 3775-29-9 ]
  • [ 120686-00-2 ]
  • [ 185741-49-5 ]
YieldReaction ConditionsOperation in experiment
50% A chiral ligand according to Formula (13) (2.13 g, 2 mol %), allyl palladiumchloride dimer (0.56 g, 1 mol %), and acetone (140 ml) were combined and stirred at 20-25 C. for 1 hour under a nitrogen atmosphere. To the mixture was added 2-methylene-1,3-propanediol diacetate (26.2 ml, 1.0 equivalent) and 35 ml of acetone and the new mixture was maintained at the same temperature for 1 hour. A mixture of the purified keto ester of Formula (5) (35 g, 1.0 equivalent), 1,1,3,3-tetramethyl guanidine (42 ml, 2.2 equivalents), and acetone (175 ml) was added to the above solution in lots over a period of 30 minutes at 20-25 C. The resulting mixture was then stirred at the same temperature for 1 hour under a nitrogen atmosphere. A sample for chiral HPLC indicated <1% starting material (keto ester) remained. Acetone was then distilled off under vacuum at 40-45 C. to obtain a crude material. The Crude material was passed through silica gel column and eluted with hexane and ethyl acetate mixtures to remove catalyst and ligand. The fractions containing product were collected and the solvent was distilled completely to yield pure product of the compound of Formula (6) (35 g, 82% yield, HPLC purity of 78%). This crude product (35 g) was stirred with isopropyl alcohol (140 ml) at 20-25 C. for 30 minutes. The obtained solid was filtered and washed with isopropyl alcohol (17.5 ml), and the material was dried under vacuum for 2-3 hours at 35-40 C. to get pure product as a white solid (21 g, 50% yield, HPLC purity of 97.5%).
 

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