Toluene → HCID 10918670, compound

HRID 382822Notes

Reaction equation

HRID 382822 reaction equation
[N+](=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-].[C:9]([C:22]1[C:26]([CH3:27])=[CH:25][N:24]([CH2:28][C:29]2[CH:30]=[C:31]([CH:37]=[CH:38][CH:39]=2)/[CH:32]=[CH:33]/[C:34]([O-:36])=[O:35])[C:23]=1[CH3:40])(=[O:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[C:41]1(C)C=CC=C[CH:42]=1>[Cu]>[C:9]([C:22]1[C:26]([CH3:27])=[C:25]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:24]([CH2:28][C:29]2[CH:30]=[C:31]([CH:37]=[CH:38][CH:39]=2)/[CH:32]=[CH:33]/[C:34]([O:36][CH2:41][CH3:42])=[O:35])[C:23]=1[CH3:40])(=[O:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 1140TolueneHCID 12192Ethyl diazoacetate2×HCID 18362062HCID 18362062, compound

Product 1

HCID 10918670HCID 10918670, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

0.24 ml of ethyl diazoacetate is added in portions each of 0.08 ml over the course of 15 min to a stirred solution of 233 mg (0.5 mmol) of (E)-3-[(3-dodecanoyl-2,4-dimethylpyrrol-1-yl)methyl]cinnamate in 3 ml of absol. Toluene at a bath temperature of 115-120° C. After each of these additions of ethyl diazoacetate a spatula tip of copper powder is added. The mixture is then heated for a further 5 min. After cooling and after addition of a little petroleum ether, the complete mixture is loaded onto a silica gel column; elution takes place with petroleum ether/ethyl acetate 9+1. The product fractions are concentrated, leaving a waxy substance.

Workup

  1. customtemperature of 115-120° C
  2. temperatureThe mixture is then heated for a further 5 min
  3. temperatureAfter cooling
  4. washelution
  5. concentrationThe product fractions are concentrated
  6. customleaving a waxy substance

Sources & evidence

ORD record
ord-e6aeb1fe30724defa89ed9bb8f9fb65f
Source dataset
uspto-grants-2001_10
Patent number
US06310217B1

Reaction notes

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