Hydrochloric Acid → 4-t-Butyl 2,2-diethyl 1-phenyl-2,2,4-butanetricarboxylate

HRID 1655747Notes

Reaction equation

HRID 1655747 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[C:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:22])[CH:20]=[CH2:21].C1CCN2C(=NCCC2)CC1.Cl>C(#N)C>[C:12]1([CH2:11][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:18])([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:21][CH2:20][C:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 15458tert-Butyl acrylateHCID 69090Diethyl 2-benzylpropanedioateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 678766354-t-Butyl 2,2-diethyl 1-phenyl-2,2,4-butanetricarboxylateYield 97.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.5 g (10 mmol) of benzylmalonic acid diethyl ester and 1.45 ml (10 mmol) of t-butyl acrylate in 5 ml of acetonitrile were treated with 1.49 ml of DBU and stirred at room temperature for 6 hours. Thereafter, the mixture was poured into dilute hydrochloric acid (pH 2), extracted with ether, the organic phase was washed with a small amount of water, dried over sodium sulfate and the solvent was removed under reduced pressure. There were obtained 3.7 g (97%) of 4-t-butyl 2,2-diethyl 1-phenyl-2,2,4-butanetricarboxylate as a pale yellow oil which was used directly in the next step.

Workup

  1. extractionextracted with ether
  2. washthe organic phase was washed with a small amount of water
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d5501e651957400fac23d0127f887c4e
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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