Sulfuric Acid → Ethyl 6-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate

HRID 2078056Notes

Reaction equation

HRID 2078056 reaction equation
OS(O)(=O)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:28])([CH3:27])[C:14]([CH:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17](OCC)=[O:18])=[O:15])=[CH:9][CH:8]=1>>[F:6][C:7]1[CH:12]=[C:11]2[C:10](=[CH:9][CH:8]=1)[C:13]([CH3:27])([CH3:28])[C:14](=[O:15])[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:17]2[OH:18]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 67099824Diethyl 2-(2-(4-fluorophenyl)-2-methylpropanoyl)malonate

Product 1

HCID 67099013Ethyl 6-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylateYield 88%

Procedure

To 5 mL concentrated H2SO4 stirred at 0° C., was slowly added diethyl 2-(2-(4-fluorophenyl)-2-methylpropanoyl)malonate (1.6 g, 4.9 mmol). The reaction was stirred at 0° C. to room temperature for 1 hour, M+1=279. The resulting mixture was poured into 100 g crushed ice and extracted with EtOAc (3×50 mL). The combined organic layers were washed with H2O (20 mL), brine (20 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by column chromatography eluting with 20% EtOAc/hexane to give 1.2 g of the product as pale yellow solid. MS m/e=279 (M+H)+.

Workup

  1. additionThe resulting mixture was poured into 100 g
  2. customcrushed ice
  3. extractionextracted with EtOAc (3×50 mL)
  4. washThe combined organic layers were washed with H2O (20 mL), brine (20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography
  8. washeluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-c19a2b1a28b4431496ea206614c75264
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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