Acetic Acid → Methyl 3-(2,6-dichlorophenyl)-2-[3-[2-[[2-(tritylamino)ethoxy]methyl]phenyl]propanoyl]-2-propenoate

HRID 480999Notes

Reaction equation

HRID 480999 reaction equation
[O:1]=[C:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][O:17][CH2:18][CH2:19][NH:20][C:21]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5].[Cl:40][C:41]1[CH:48]=[CH:47][CH:46]=[C:45]([Cl:49])[C:42]=1[CH:43]=O.C(O)(=O)C.N1CCCCC1>C1C=CC=CC=1>[CH3:7][O:6][C:4](=[O:5])[C:3]([C:2](=[O:1])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][O:17][CH2:18][CH2:19][NH:20][C:21]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[CH:43][C:42]1[C:41]([Cl:40])=[CH:48][CH:47]=[CH:46][C:45]=1[Cl:49]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 67372,6-DichlorobenzaldehydeHCID 8082PiperidineHCID 18765860Methyl 3-oxo-5-[2-[[2-(tritylamino)ethoxy]methyl]phenyl]pentanoate

Product 1

HCID 69684722Methyl 3-(2,6-dichlorophenyl)-2-[3-[2-[[2-(tritylamino)ethoxy]methyl]phenyl]propanoyl]-2-propenoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of methyl 3-oxo-5-[2-[[2-(tritylamino)ethoxy]methyl]phenyl]pentanoate (3.33 g, 6.38 mmol), 2,6-dichlorobenzaldehyde (1.12 g, 6.38 mmol), acetic acid (0.5 ml), piperidine (0.5 ml) and benzene (50 ml) was stirred for 4 hours at reflux temperature azeotropically. The reaction mixture was quenched with water (40 ml) and the whole was extracted with Et2O (20 ml×2). The combined extracts were washed with brine, dried over MgSO4, and concentrated in vacuo to afford the titled compound as a yellow oil. (quant.)

Workup

  1. temperatureat reflux temperature azeotropically
  2. customThe reaction mixture was quenched with water (40 ml)
  3. extractionthe whole was extracted with Et2O (20 ml×2)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe88ccb6eb3348d79aef1ac1f7c21ae0
Source dataset
uspto-grants-2003_11
Patent number
US06653313B2

Reaction notes

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