HCID 67099592, compound → HCID 67099365, compound

HRID 2078123Notes

Reaction equation

HRID 2078123 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)([CH3:22])[C:9]([CH:11]([C:17]([O:19]CC)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])=[CH:4][CH:3]=1>OS(O)(=O)=O>[Cl:29][C:26]1[CH:25]=[C:24]2[C:23](=[CH:28][CH:27]=1)[C:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)([CH3:22])[C:9](=[O:10])[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:17]2[OH:19]

Participants

3

Reactant 1

HCID 67099592HCID 67099592, compound

Product 1

HCID 67099365HCID 67099365, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of diethyl 2-(2,2-bis(4-chlorophenyl)propanoyl)malonate (2.00 g, 4.57 mmol) in H2SO4, 36N (10.0 mL, 180 mmol) in a 500 mL round bottom flask was stirred at 25° C. for 30 minutes. The reaction was quenched by adding 400 mL of ice and 100 mL of EtOAc and then stirring for 15 minutes. The layers were separated, and the aqueous solution was extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine (100 mL). The organic layer was then dried over MgSO4 and concentrated in vacuo to give 2.24 g of crude product which was purified by flash column chromatography (silica, 0-100% DCM in hexane) to give the title compound (1.448 g). MS m/e=391 (M+H)+.

Workup

  1. customThe reaction was quenched
  2. additionby adding 400 mL of ice and 100 mL of EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous solution was extracted with EtOAc (2×100 mL)
  5. washThe combined organic layers were washed with brine (100 mL)
  6. dry with materialThe organic layer was then dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto give 2.24 g of crude product which
  9. customwas purified by flash column chromatography (silica, 0-100% DCM in hexane)

Sources & evidence

ORD record
ord-73b0e04e90884dfeaec7fe09c51ae3df
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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