Hydrochloric Acid → HCID 86605434, compound

HRID 1437214Notes

Reaction equation

HRID 1437214 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14].[C:21](OCC)(=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].Cl>O1CCCC1>[CH2:25]([O:24][C:22](=[O:23])[C:21](=[O:27])[CH:12]([F:11])[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14])[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 99472-Fluoro-1-phenylethan-1-oneHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 86605434HCID 86605434, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.0 M Lithium bis(trimethylsilyl)amide in tetrahydrofuran (13 mL) was added dropwise to α-fluoroacetophenone (1.64 g) in tetrahydrofuran (35 mL) at α-78° C., followed by stirring for 45 minutes. Diethyl oxalate (1.77 mL) was added to the reaction mixture, followed by stirring for 30 minutes. The mixture was further stirred at 0° C. for 1 hour. The resultant mixture was neutralized with 1M aqueous solution of hydrochloric acid. The reaction mixture was partitioned between water and chloroform. Subsequently, the aqueous layer was extracted with chloroform. The organic layers were combined, and washed with saturated brine, and then dried over sodium sulfate anhydrate. The mixture was subjected to filtration, and the solvent was evaporated under reduced pressure, to thereby give 3-fluoro-4-phenyl-2,4-dioxobutanoic acid ethyl ester as an oily substance (0.753 g, 27%).

Workup

  1. stirringby stirring for 30 minutes
  2. stirringThe mixture was further stirred at 0° C. for 1 hour
  3. customThe reaction mixture was partitioned between water and chloroform
  4. extractionSubsequently, the aqueous layer was extracted with chloroform
  5. washwashed with saturated brine
  6. dry with materialdried over sodium sulfate anhydrate
  7. filtrationThe mixture was subjected to filtration
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-19eb0c44fe0e431ba9431112cea67405
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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