Ethyl Acetate → HCID 20268268, compound

HRID 2413275Notes

Reaction equation

HRID 2413275 reaction equation
C[Li].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=2[C:20](O)=[O:21])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:27](OCC)(=O)C.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=2[C:20](=[O:21])[CH3:27])=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 13749492HCID 13749492, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 20268268HCID 20268268, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyllithium (280 ml, 1M in ether) was added slowly to a solution of 31.9 g (0.1 mole) of 2-(4-benzyloxyphenylamino)benzoic acid (Example 2, part a) in 300 ml of tetrahydrofuran cooled to 0°-5° C. The reaction mixture was stirred at 0°-5° C. for 75 minutes. Ethyl acetate was then added and the mixture poured into a mixture of ice and saturated ammonium chloride solution. The aqueous suspension was extracted with ether, the ether extracts dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from isopropyl alcohol to give 24 g of 1-[2-(4-benzyloxyphenylamino)phenyl]ethanone.

Workup

  1. temperaturecooled to 0°-5° C
  2. extractionThe aqueous suspension was extracted with ether
  3. dry with materialthe ether extracts dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-5116f50aecef46f3aa403f20fdfdb65f
Source dataset
uspto-grants-1985_01
Patent number
US04496590

Reaction notes

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