Sodium Chloride → HCID 131722940, compound

HRID 382826Notes

Reaction equation

HRID 382826 reaction equation
[CH3:1][C:2]1[N:3]([CH2:27][C:28]2[CH:38]=[CH:37][C:31](/[CH:32]=[CH:33]/[C:34]([O-:36])=[O:35])=[CH:30][CH:29]=2)[CH:4]=[C:5]([CH3:26])[C:6]=1[C:7](=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[C:39]([O:43][CH3:44])(=[O:42])[CH:40]=[CH2:41].[N+]([C:48]1C=CC=C[CH:49]=1)([O-])=O.[Na+].[Cl-]>>[CH3:44][O:43][C:39]([CH2:40][CH2:41][C:4]1[N:3]([CH2:27][C:28]2[CH:29]=[CH:30][C:31](/[CH:32]=[CH:33]/[C:34]([O:36][CH2:48][CH3:49])=[O:35])=[CH:37][CH:38]=2)[C:2]([CH3:1])=[C:6]([C:7](=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:5]=1[CH3:26])=[O:42]

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 7294Methyl AcrylateHCID 7416NitrobenzeneHCID 18362051HCID 18362051, compound

Product 1

HCID 131722940HCID 131722940, compound

Procedure

0.1 ml of BF3/ethyl ether complex is added to a solution of 275 mg (0.5 mmol) of (E)-4-[(2,4-dimethyl-3-octadecanoylpyrrol-1-yl)methyl]cinnamate and 0.25 ml of methyl acrylate in 5 ml of absol. nitrobenzene. The mixture is stirred at room temperature for 24 h. Addition of saturated NaCl solution is followed by extraction with ether. After drying over Na2SO4, the solvent is distilled off, and the residue is purified by CC (silica gel, 1. petroleum ether/ethyl acetate 9+1, 2. petroleum ether/ethyl acetate 8+2). The product fractions are concentrated; the remaining oil crystallizes after some time.

Workup

  1. extractionis followed by extraction with ether
  2. dry with materialAfter drying over Na2SO4
  3. distillationthe solvent is distilled off
  4. customthe residue is purified by CC (silica gel, 1. petroleum ether/ethyl acetate 9+1, 2. petroleum ether/ethyl acetate 8+2)
  5. concentrationThe product fractions are concentrated
  6. customthe remaining oil crystallizes after some time

Sources & evidence

ORD record
ord-052e9c0c37fa4422bbd3829db165856d
Source dataset
uspto-grants-2001_10
Patent number
US06310217B1

Reaction notes

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