Ethoxalyl chloride → HCID 67191294, compound

HRID 546264Notes

Reaction equation

HRID 546264 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH2:5]([O:7][C:8](=[O:12])[C:9](Cl)=[O:10])[CH3:6].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20][CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>C(Cl)Cl>[CH2:5]([O:7][C:8](=[O:12])[C:9]([C:18]1[CH:17]=[CH:16][C:15]([S:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[C:14]([Cl:13])[CH:19]=1)=[O:10])[CH3:6]

Participants

5

Reactant 3

HCID 20884Ethoxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 67188050HCID 67188050, compound

Product 1

HCID 67191294HCID 67191294, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In a round bottom flask is placed methylene chloride (100 mL) and aluminum trichloride (1.39 equiv) and it is cooled to 0° C. in an ice bath. To this solution is then added dropwise chloro-oxo-acetic acid ethyl ester (1.09 equiv.) keeping the temperature of the solution below 5° C. and it is then stirred for 30 min at 0° C. After this time a solution of 1-chloro-2-cyclopentylsulfanyl-benzene (50.0 mmol) in methylene chloride (5 mL) is added dropwise while keeping the temperature of the solution below 5° C. The ice bath is then removed and the reaction is allowed to warm up to 25° C. and is stirred for 3 h. The reaction is then cooled back down to 0° C. in an ice bath and ice water (20 mL) is then added dropwise keeping the temperature of the solution below 20° C. It is then stirred for 15 min and then transferred to a separatory funnel and separated. The organic phase is then washed with water (2×25 mL), saturated aqueous sodium bicarbonate solution (2×25 mL) and water (25 mL) and then dried over magnesium sulfate, filtered and concentrated in vacuo to afford (3-chloro-4-cyclopentylsulfanyl-phenyl)-oxo-acetic acid ethyl ester.

Workup

  1. customIn a round bottom flask is placed
  2. customthe temperature of the solution below 5° C. and it
  3. customthe temperature of the solution below 5° C
  4. customThe ice bath is then removed
  5. temperatureto warm up to 25° C.
  6. stirringis stirred for 3 h
  7. temperatureThe reaction is then cooled back down to 0° C. in an ice bath
  8. additionice water (20 mL) is then added dropwise
  9. customthe temperature of the solution below 20° C
  10. stirringIt is then stirred for 15 min
  11. customtransferred to a separatory funnel
  12. customseparated
  13. washThe organic phase is then washed with water (2×25 mL), saturated aqueous sodium bicarbonate solution (2×25 mL) and water (25 mL)
  14. dry with materialdried over magnesium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10eac3c734854f76a06d39f47f0fb485
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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