Sulfuric Acid → HCID 67099630, compound

HRID 1868751Notes

Reaction equation

HRID 1868751 reaction equation
[CH3:1][C:2]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)([CH3:16])[C:3]([CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8]CC)=O)=[O:4].OS(O)(=O)=O>>[OH:8][C:6]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([F:26])([F:24])[F:25])=[CH:20][CH:21]=2)[C:2]([CH3:16])([CH3:1])[C:3](=[O:4])[C:5]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 67099899HCID 67099899, compound

Product 1

HCID 67099630HCID 67099630, compoundYield 43.5%

Procedure

Diethyl 2-(2-methyl-2-(3-(trifluoromethyl)phenyl)propanoyl)malonate (2.80 g, 7.5 mmol) was added to H2SO4 (40 mL, 237 mmol), and the mixture was stirred at room temperature for 1 hour. Ice (H2O) was added, and the aqueous mixture was extracted with EtOAc (2×). The combined organic layers were washed with water (2×) and brine, dried (MgSO4), and concentrated in vacuo to give the crude compound as a yellow oil. The crude oil was purified by silica flash chromatography (0-50% DCM/hexane) to give the desired compound as a yellow semi-solid (1.07 g). MS (m/e)=329.1 (M+H)+.

Workup

  1. additionIce (H2O) was added
  2. extractionthe aqueous mixture was extracted with EtOAc (2×)
  3. washThe combined organic layers were washed with water (2×) and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude compound as a yellow oil
  7. customThe crude oil was purified by silica flash chromatography (0-50% DCM/hexane)

Sources & evidence

ORD record
ord-6e5be311677f4fbea36a062784d50363
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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