Triethylamine → 2,2-Diphenylethyl 3-oxobutanoate

HRID 1297019

Reaction equation

HRID 1297019 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH2:23]=[C:24]1[O:28][C:26](=[O:27])[CH2:25]1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:26]([O:9][CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:27])[CH2:25][C:24]([CH3:23])=[O:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12661DiketeneHCID 74662beta-Phenylphenethyl alcoholHCID 516892Sodium Bicarbonate

Product 1

HCID 40765052,2-Diphenylethyl 3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

500 mg (2.52 mmol) of 2,2-diphenylethanol was dissolved in 10 ml of toluene. 382 mg (3.78 mmol) of triethylamine was added to the obtained solution, and they were stirred at room temperature for 1 hour. 386 mg (3.03 mmol) of diketene was added to the obtained mixture under cooling with ice, and then they were stirred under heating at 100° C. for 2 hours. After the addition of saturated aqueous sodium hydrogencarbonate solution followed by the extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the unpurified title compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringthey were stirred
  3. temperatureunder heating at 100° C. for 2 hours
  4. extractionfollowed by the extraction with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-16d1b5b64c60448a9becba0e62027330
Source dataset
uspto-grants-2007_07
Patent number
US07247645B2

Linked notes

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