Water → HCID 70295804, compound

HRID 1870827Notes

Reaction equation

HRID 1870827 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:12])[C:9](=[O:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+].[C:21](OCC)(=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:12])[C:9](=[O:11])[CH:10]=[C:21]([OH:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 10037388HCID 10037388, compound

Product 1

HCID 70295804HCID 70295804, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

3-(2-Fluoro-biphenyl-4-yl)-butan2-one (Japanese Patent Unexamined Publication No. 54-144347) (116 mg) was dissolved in toluene (2 ml), followed by adding thereto sodium hydride (29 mg, 60% oily), and the mixture was stirred at room temperature for 1 hour. Then, diethyl oxalate (105 mg) was added and the resulting mixture was stirred at 40° C. for 3 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate, and the extract solution was washed with water and dried. The solvent was distilled off under reduced pressure and the residue was purified by a silica gel column chromatography to obtain the desired compound (163 mg).

Workup

  1. additionby adding
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract solution was washed with water
  4. customdried
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-e0f9e46adc364cb4a0808bde7c344e35
Source dataset
uspto-grants-2000_08
Patent number
US06100260

Reaction notes

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