Diketene → HCID 70413510, compound

HRID 979830Notes

Reaction equation

HRID 979830 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[C:7]([C:9]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=1)([CH:19]([CH3:21])[CH3:20])[CH2:10][CH2:11][CH2:12][N:13]([CH2:15][CH:16]([CH3:18])[OH:17])[CH3:14])#[N:8]>C1(C)C=CC=CC=1>[C:4]([O:17][CH:16]([CH3:18])[CH2:15][N:13]([CH2:12][CH2:11][CH2:10][C:9]([C:7]#[N:8])([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=1)[CH:19]([CH3:20])[CH3:21])[CH3:14])(=[O:5])[CH2:3][C:2]([CH3:1])=[O:6]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 20223068HCID 20223068, compound

Product 1

HCID 70413510HCID 70413510, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

2.7 ml of diketene was added, over 10 minutes, to a solution of 11.36 g of the compound prepared in Example 2 in 10 ml of toluene at 80° C. When the exothermic reaction was over, the reaction mixture was heated for 2 hours at 80° C. and, after cooling, it was evaporated to dryness in vacuo. The oily residue was then purified by silica gel column chromatography using ehtyl acetate containing decreasing amounts of petroleum ether as eluent. The unitary TLC fractions (chloroform:methanol 95:5 by volume) were evaporated to dryness in vacuo to give 11.61 g of the title compound as an oil.

Workup

  1. customWhen the exothermic reaction
  2. temperatureafter cooling
  3. customit was evaporated to dryness in vacuo
  4. customThe oily residue was then purified by silica gel column chromatography
  5. customThe unitary TLC fractions (chloroform:methanol 95:5 by volume) were evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-a2c2cf3b8eb94cb28aae7f189096fea9
Source dataset
uspto-grants-1987_01
Patent number
US04634712

Reaction notes

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