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Chemical Structure| 3744-80-7 Chemical Structure| 3744-80-7

Structure of 3744-80-7

Chemical Structure| 3744-80-7

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Product Details of [ 3744-80-7 ]

CAS No. :3744-80-7
Formula : C6H7ClO
M.W : 130.57
SMILES Code : O=C(Cl)C1CC=CC1
MDL No. :MFCD27950092

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Application In Synthesis of [ 3744-80-7 ]

* 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 [ 3744-80-7 ]

[ 3744-80-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 3744-80-7 ]
  • [ 21622-01-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In ethanol; dichloromethane; for 12.5h;Inert atmosphere; Cooling with ice; A round-bottomed flask equipped with astir bar was charged with 3-cyclopentenecarboxylic acid (S40) (2.11 g, 18.8 mmol). The flask was flushed with N2 and placed in an ice bath. Distilled CH2Cl2 (38 mL), oxalyl chloride (3.3mL, 37.8 mmol) and anhydrous DMF (5 drops, catalytic) were added, respectively. The reaction was stirred for 4.5 h at 0 C, whereupon the ice bath was removed. The reaction was allowed to stir for an additional 1.5 h at room temperature during which time the color turned to brown. Solvent was removed from the reaction mixture via rotary evaporation. The acid chloride S41 was dissolved in distilled CH2Cl2 (38 mL) under N2, and the reaction was placed in an ice bath. 200 proof EtOH (3.2 mL, 56.7 mmol) and anhydrous triethylamine (2.9 mL, 20.8 mmol) were added simultaneously. The ice bath was allowed to expire as the reaction was stirred for 12.5 h. The reaction mixture was washed with H2O (50 mL), saturated NaHCO3 (50 mL), and brine, respectively. After drying over MgSO4, solvent was removed via rotary evaporation. The crude product was purified by flash chromatography on silica gel (10% EtOAc/hexanes). The fractions containing the volatile product were concentrated via rotary evaporation, and the remaining solvent was distilled away via Kügelrohr distillation at 51 mmHg. Isolated 1.49 g of a clearliquid. Observed <1% by mass CH2Cl2 and <1% by mass EtOAc by 1H NMR analysis. The corrected yield was 56%.
 

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