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Chemical Structure| 170115-18-1 Chemical Structure| 170115-18-1

Structure of 170115-18-1

Chemical Structure| 170115-18-1

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Product Details of [ 170115-18-1 ]

CAS No. :170115-18-1
Formula : C11H14O4
M.W : 210.23
SMILES Code : O=C(OC(C)(C)C)CC(C1=CC=CO1)=O

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Application In Synthesis of [ 170115-18-1 ]

* 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 [ 170115-18-1 ]

[ 170115-18-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 540-88-5 ]
  • [ 95091-92-2 ]
  • [ 170115-18-1 ]
YieldReaction ConditionsOperation in experiment
General procedure: To a stirred solution of acid (1 equiv) in CH2Cl2 (for a solution of0.1 mol L1) were added oxalyl chloride [(COCl)2; 1.25 equiv] and DMF (0.004 equiv) at room temperature. After 1.5 h, the solventand the excess oxalyl chloride were removed by evaporation under vacuum. CH2Cl2 (for a solution of 0.1 mol L1), N,O-dimethylhydroxylamine (1.4 equiv), and Et3N (3 equiv) were then successively added at room temperature. After 2 h, the reaction was quenched at room temperature with a saturated solution of NaHCO3 and the mixture extracted twice with CH2Cl2. The combined organic layers were then washed with a saturated solution of NH4Cl and brine. The organic layer was then dried with anhydrous MgSO4, filtered, and concentrated under vacuum to afford the crude Weinreb amine.To a stirred solution of diisopropylamine (DIPA; 3 equiv) in THF (for a solution of 0.1 mol L1) was added n-Butyl lithium (nBuLi,1.2 M in hexane, 3.1 equiv) at -78 C. After 30 min at 0 C, the medium was recooled to -78 C and freshly distilled tBu acetate (3 equiv) was added. After 30 min at -78 C, crude Weinreb amide (1 equiv) was added at this temperature. After 1 h, the reaction was quenched at room temperature with a saturated solution of NaHCO3 and the mixture extracted twice with EtOAc. The combined organic layers were then washed with a saturated solution of NH4Cl. The organic layer was then dried with anhydrous MgSO4, filtered, and concentrated under vacuum to afford the crude tert-butyl ester. To a stirred solution of tert-butyl ester (1 equiv) in acetone (10 equiv) were added acetic anhydride (15 equiv) and sulfuric acid (1 equiv) at 0 C. The medium was then warmed slowly to room temperature over 10 min. After 45 min, the reaction was quenched at room temperature with an aqueous solution containing sodium carbonate (30 equiv) and EtOAc (100 mL) was added.The biphasic medium was then stirred for 40 min (hydrolysis ofthe remaining acetic anhydride) and the aqueous layer was extracted twice with EtOAc. The combined organic layers were then washed with a saturated solution of NH4Cl. The organic layer was dried with anhydrous MgSO4, filtered and concentrated under vacuum. The crude residue was finally purified by flash chromatography silica gel using an appropriate gradient of a cyclohexane/EtOAc mixture as eluent to give the desired dioxinone.
 

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