Hydrochloric Acid → HCID 21846234, compound

HRID 619293Notes

Reaction equation

HRID 619293 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[C:5]([C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=1.[H-].[Na+].[C:18](OCC)(=[O:22])[CH:19]([CH3:21])[CH3:20].Cl>O1CCOCC1>[F:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[C:5]([C:13](=[O:15])[CH2:14][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7342Ethyl isobutyrateHCID 24758Sodium hydrideHCID 21846387HCID 21846387, compound

Product 1

HCID 21846234HCID 21846234, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(4,7-difluoronaphth-1-yl)-ethanone (0.150 g, 0.72 mmol) was dissolved in dry dioxane (1 mL) and cooled to 0° C. Sodium hydride (0.145 g, 3.6 mmol, 60 wt. % dispersion) was added and the reaction mixture was stirred for 1 hour at room temperature. Ethyl isobutyrate (1.0 mL, 7.2 mmol) was added in one portion and the solution was heated to reflux for 15 minutes. After cooling to room temperature, the reaction mixture was poured onto 10% aqueous hydrochloric acid and extracted with methylene chloride. The organic layer was dried over sodium sulfate and purified by column chromatography to give 1-(4,7-difluoronaphth-1-yl)-4-methylpentane-1,3-dione (0.120 g, 72%).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 15 minutes
  3. temperatureAfter cooling to room temperature
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-5e9e477c1de14e5fa956725897f4539f
Source dataset
uspto-grants-1999_09
Patent number
US05958934

Reaction notes

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