Acetic Acid → HCID 19072491, compound

HRID 1955732Notes

Reaction equation

HRID 1955732 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:23])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:11][CH:10]=1.O.C(O)(=O)C>C1C=CC=CC=1.C(OCC)C.C1COCC1.C(OCC)C>[CH3:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([OH:23])[C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 11106890HCID 11106890, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 19072491HCID 19072491, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 22174802Benzene etherSolvent

Procedure

30 ml of a 2M solution (60 mol) of phenyllithium in benzene/diethyl ether (3:1) are added dropwise at 0° C. with stirring to 13.2 g (60 mmol) of tert-butyl 2-(4-methyl-phenyl)-2-oxo-acetate under argon in 70 ml of THF and the mixture is stirred at room temperature for a further 1 h. The mixture is diluted with 80 ml of diethyl ether, poured into 150 ml of water with stirring, neutralised with 1N acetic acid and extracted three times with diethyl ether. The combined organic phases are dried over sodium sulphate and concentrated, and the product is chromatographed on silica gel 60 using 40-60 petroleum ether/ethyl acetate (4:1).

Workup

  1. extractionextracted three times with diethyl ether
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated
  4. customthe product is chromatographed on silica gel 60 using 40-60 petroleum ether/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-a67b9354a5844605be97f0536dfbf6ab
Source dataset
uspto-grants-1998_07
Patent number
US05776964

Reaction notes

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