p-Toluenesulfonic acid → 3-(3-Chlorophenyl)-2-[(2-cyclohexylethoxy)acetyl]-2-propenoic acid 3,3-diphenylpropyl ester

HRID 1727942Notes

Reaction equation

HRID 1727942 reaction equation
[C:1]1([CH:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:8][CH2:9][O:10][C:11](=[O:25])[CH2:12][C:13](=[O:24])[CH2:14][O:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH:36]=O.N1CCCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:1]1([CH:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:8][CH2:9][O:10][C:11](=[O:25])[C:12]([C:13](=[O:24])[CH2:14][O:15][CH2:16][CH2:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)=[CH:36][C:35]2[CH:38]=[CH:39][CH:40]=[C:33]([Cl:32])[CH:34]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8082PiperidineHCID 114773-ChlorobenzaldehydeHCID 690630434-(2-Cyclohexylethoxy)-3-oxobutanoic acid 3,3-diphenylpropyl ester

Product 1

HCID 690677113-(3-Chlorophenyl)-2-[(2-cyclohexylethoxy)acetyl]-2-propenoic acid 3,3-diphenylpropyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.23 g (2.90 mmol) of 4-(2-cyclohexylethoxy)-3-oxobutanoic acid 3,3-diphenylpropyl ester, 0.33 ml (2.91 mmol) of 3-chlorobenzaldehyde, 0.05 ml (0.51 mmol) of piperidine and catalytic amount of p-toluenesulfonic acid were refluxed in 20 ml of benzene removing water for 1.5 hours. After adding ethyl acetate, the organic layer was washed with 1 N hydrochloric acid and saturated aqueous sodium hydrogencarbonate solution, and dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain the title compound.

Workup

  1. customremoving water for 1.5 hours
  2. additionAfter adding ethyl acetate
  3. washthe organic layer was washed with 1 N hydrochloric acid and saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2b8e7586b7ed492e88976413a2bfdf7a
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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