HCID 67099769, compound → HCID 67099664, compound

HRID 1868681Notes

Reaction equation

HRID 1868681 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([CH3:24])([CH3:23])[C:10]([CH:12]([C:18]([O:20]CC)=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:11]>OS(O)(=O)=O>[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]2[C:3]=1[C:9]([CH3:24])([CH3:23])[C:10](=[O:11])[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:18]2[OH:20]

Participants

3

Reactant 1

HCID 67099769HCID 67099769, compound

Product 1

HCID 67099664HCID 67099664, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To 20 mL concentrated H2SO4 stirred at room temperature, was added diethyl 2-(2-(2-fluoro-3-hydroxyphenyl)-2-methylpropanoyl)malonate (3.6 g, 11 mmol). The mixture was stirred at room temperature for 2 hours, M+1=295. The mixture was then poured into 100 g crushed ice and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 10-30% EtOAc/hexane to give 2.9 g of the title compound as a pale yellow solid. MS (m/z)=295 (M+H)+.

Workup

  1. additionThe mixture was then poured into 100 g
  2. customcrushed ice
  3. extractionextracted with EtOAc (3×50 mL)
  4. washThe combined organic layers were washed with brine (20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography
  8. washeluting with 10-30% EtOAc/hexane

Sources & evidence

ORD record
ord-ca42a0782e8d4c599fc146b1d875f339
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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