Benzene → HCID 86657328, compound

HRID 1517502Notes

Reaction equation

HRID 1517502 reaction equation
[H-].[Na+].CCOP([O:11][C:12]([CH3:14])=[O:13])(OCC)=O.[CH2:15]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:18](=O)[CH2:17][CH2:16]1.[Cl-].[NH4+].[CH:29]1C=CC=C[CH:30]=1>>[CH:24]1[C:25]2[CH2:26][CH2:15][CH2:16][CH2:17][C:18](=[CH:14][C:12]([O:11][CH2:29][CH3:30])=[O:13])[C:20]=2[CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 5

HCID 241Benzene3×HCID 18353Acetyl diethyl phosphateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 70003Benzosuberone

Product 1

HCID 86657328HCID 86657328, compound

Conditions

Temperature
0 °C

Procedure

A suspension of sodium hydride (60%, 2.25 g) in anhydrous benzene (100 ml) was slowly added with a solution of diethyl phosphonoacetate (14.0 g) in anhydrous benzene (20 ml) at 0° C., and the mixture was stirred at 0° C. for 15 minutes. The mixture was added with a solution of 1-benzosuberone (5.00 g) in anhydrous benzene (30 ml), and the mixture was stirred at 0° C. for 15 minutes, and then refluxed overnight by heating. The reaction mixture was left to cool and then added with saturated aqueous ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:200) to quantitatively obtain the title compound.

Workup

  1. stirringthe mixture was stirred at 0° C. for 15 minutes
  2. temperaturerefluxed overnight
  3. temperatureby heating
  4. waitThe reaction mixture was left
  5. temperatureto cool
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed successively with water and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationThe organic layer was concentrated under reduced pressure
  10. customthe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:200)

Sources & evidence

ORD record
ord-995173a51dcb49f9a46ba6fc2b6a98a5
Source dataset
uspto-grants-2012_07
Patent number
US08232300B2

Reaction notes

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