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Chemical Structure| 1070-13-9 Chemical Structure| 1070-13-9

Structure of 1070-13-9

Chemical Structure| 1070-13-9

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Product Details of [ 1070-13-9 ]

CAS No. :1070-13-9
Formula : C6H10O
M.W : 98.14
SMILES Code : O=CC(CCC)=C

Safety of [ 1070-13-9 ]

Application In Synthesis of [ 1070-13-9 ]

* 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 [ 1070-13-9 ]

[ 1070-13-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1070-13-9 ]
  • [ 120686-00-2 ]
  • C18H23NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N,N,N',N'-tetramethylguanidine; In dichloromethane; at 20℃; for 12h; General procedure: To a solution of beta-ketoester 10a (1 mmol), 1,1,3,3-tetramethylguanidine (26 muL, 0.2 mmol) in dichloromethane (2.5 mL) was added alpha,beta-unsaturated aldehyde 11a (10 mmol). The reaction mixture was stirred at room temperature for 12 h and then the solvent was removed under vacuum. The residue was purified by silica gel chromatography to yield the bridged product 12a. To a solution of the alcohol 12a (0.5 mmol) and trimethylamine (690 muL, 5 mmol) in 2.5 mL of dichloromethane was added dropwise mesyl chloride (154 muL, 2 mmol) and a catalytic amount of DMAP at room temperature. The solution was stirred for 12 h at room temperature, and then diluted with dichloromethane, washed with satd aq NH4Cl, dried and concentrated. The above crude product was dissolved in HOAc (10 mL), and NaOAc (48 mg, 0.6 mmol) was added. The solution was heated to reflux for 24 h. After concentration in vacuum, the residue was treated with satd aq NaHCO3, and extracted with ethyl acetate. The combined organic extracts was washed with brine and dried. After concentration in vacuum, the residue was purified by silica gel chromatography to give rac-13a.
  • 2
  • [ 1070-13-9 ]
  • [ 120686-00-2 ]
  • C18H23NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: To a solution of beta-ketoester 10a (0.5 mmol), catalyst 8 (0.05 mmol) and PhCOOH (0.05 mmol) in toluene/dichloromethane (1:1, 0.2 M) was added alpha,beta-unsaturated aldehyde 11a (5 mmol). The reaction mixture was stirred at room temperature for the time indicated in tables. The solvent was then removed under vacuum. The residue was dissolved in dichloromethane (2.5 mL), and tetramethylguanidine (20 muL, 0.15 mmol) was added. The reaction mixture was stirred at room temperature for 12 h, and the solvent was then removed under vacuum. The residue was submitted to a short silica gel column to remove the catalyst from the bridged product 12a quickly. To a solution of the alcohol 12a, trimethylamine (690 muL, 5 mmol) and a catalytic amount of DMAP in 5 mL of dichloromethane was added dropwise mesyl chloride (154 muL, 2 mmol) at room temperature. The solution was stirred for 12 h at room temperature, and then diluted with dichloromethane. The mixture was washed with satd aq NH4Cl, dried and concentrated. The resulting crude product was dissolved in HOAc (10 mL), and NaOAc (48 mg, 0.6 mmol) was added. The solution was heated to reflux for 24 h. After concentration in vacuum, the residue was diluted with satd aq NaHCO3 and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried. After concentration in vacuum, the residue was purified by silica gel chromatography to give 13a. The procedure for the gram-scale synthesis was enlarged accordingly.
 

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