Sodium amide → HCID 18690195, compound

HRID 1872096Notes

Reaction equation

HRID 1872096 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH3:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[NH2-].[Na+].C1([O:21][C:22](=O)[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)C=CC=CC=1>O1CCCC1>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH3:12])=[CH:8][CH:9]=2)[CH2:4][CH:3]1[C:22](=[O:21])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 24533Sodium amideHCID 787875-Methoxyindan-1-oneHCID 346052Phenyl 4-methoxybenzoate

Product 1

HCID 18690195HCID 18690195, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 22.2 g (137 mmol) of 1-oxo-5-methoxyindane in tetrahydrofuran was added dropwise to a cold suspension of 11 g (274 mmol) of sodium amide in tetrahydrofuran. The resulting mixture was stirred for ten minutes and a solution of 31.3 g (137 mmol) of phenyl-4-methoxybenzoate in tetrahydrofuran was added. Cooling was discontinued and a slight exothermic reaction occurred. The mixture was stirred at ambient temperature for an additional two hours. A thick precipitate developed and the reaction mixture was poured into ice-water. The aqueous mixture was extracted with ethyl acetate. The ethyl acetate extract was evaporated to dryness to obtain 20.7 g of the title compound. mp: 160° C.-162° C.

Workup

  1. temperatureCooling
  2. customa slight exothermic reaction
  3. stirringThe mixture was stirred at ambient temperature for an additional two hours
  4. extractionThe aqueous mixture was extracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. customwas evaporated to dryness

Sources & evidence

ORD record
ord-2c51a316e25c47c6938a798dc3adaa3c
Source dataset
uspto-grants-2000_08
Patent number
US06107346

Reaction notes

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