Diisopropylamine → 5-[2-(2,5-Dimethoxyphenyl)ethenyl]-2-acetylamino benzoic acid methylester

HRID 1603539Notes

Reaction equation

HRID 1603539 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[Br-].[CH3:14][O:15][C:16]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][C:17]=1[CH2:18][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:44][O:45][C:46](=[O:59])[C:47]1[CH:52]=[C:51]([CH:53]=O)[CH:50]=[CH:49][C:48]=1[NH:55][C:56](=[O:58])[CH3:57].[Cl-].[NH4+]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH3:44][O:45][C:46](=[O:59])[C:47]1[CH:52]=[C:51]([CH:53]=[CH:18][C:17]2[CH:38]=[C:39]([O:42][CH3:43])[CH:40]=[CH:41][C:16]=2[O:15][CH3:14])[CH:50]=[CH:49][C:48]=1[NH:55][C:56](=[O:58])[CH3:57]

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 19605777(2,5-Dimethoxybenzyl)(triphenyl)phosphonium bromideHCID 544793022-Acetylamino-5-formyl-benzoic acid methylesterHCID 178418339Butyllithium

Product 1

HCID 543195135-[2-(2,5-Dimethoxyphenyl)ethenyl]-2-acetylamino benzoic acid methylester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

4.1 mmol of n-butyllithium (0.4 ml of 1.6 M solution in hexane) are added at -40° to a solution of 412 mg of diisopropylamine in 30 ml of dry tetrahydrofuran. After stirring for 30 minutes 672 mg of 2,5-dimethoxybenzyl-triphenylphosphonium bromide are added at this temperature. The suspension is stirred for another 30 minutes, cooled to -70° and treated with 300 mg of 2-acetylamino-5-formyl-benzoic acid methylester in 8 ml of absolute tetrahydrofuran. The mixture is stirred for one hour at -70° and for two hours at room temperature and then poured onto aqueous ammonium chloride solution. Extraction with ethyl acetate and evaporation yields a crude product, which is subjected to silica gel chromatography (hexane/ethyl acetate =9/1) to obtain the title compound as a mixture of the E- and Z-isomers.

Workup

  1. additionare added at this temperature
  2. temperaturecooled to -70°
  3. stirringThe mixture is stirred for one hour at -70° and for two hours at room temperature
  4. extractionExtraction
  5. customwith ethyl acetate and evaporation
  6. customyields a crude product, which

Sources & evidence

ORD record
ord-40b2ea27733b4219be27bbb475b34cd8
Source dataset
uspto-grants-1999_11
Patent number
US05990116

Reaction notes

Loading…