Pyridine → HCID 16040662, compound

HRID 899553Notes

Reaction equation

HRID 899553 reaction equation
[OH:1][C:2]1[C:3](=[O:21])[CH:4]=[C:5]([OH:20])[C:6](=[O:19])[C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].N1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:28]1([CH3:37])[CH:33]=[CH:32][CH:31]=[C:30]([C:34](Cl)=[O:35])[CH:29]=1>ClCCl>[CH3:23][C:24]1[CH:6]=[C:7]([C:2]([O:19][C:6]2[C:5](=[O:20])[CH:4]=[C:3]([O:21][C:34]([C:30]3[CH:31]=[CH:32][CH:33]=[C:28]([CH3:37])[CH:29]=3)=[O:35])[C:2](=[O:1])[C:7]=2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:1])[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 3218EmbelinHCID 743753-Methylbenzoyl chloride

Product 1

HCID 16040662HCID 16040662, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,5-dihydroxy-3-undecyl-1,4-benzoquinone (0.5 g, 1.7 mmole) in dichloromethane (20 mL) was added pyridine (0.55 mL, 6.8 mmole). To this, was added 3-toluoyl chloride (0.654 gm, 4.25 mmole) at 15-20° C. and stirred, allowed to attain 30° C. and stirring was continued for 3 h (TLC). The organic layer was extracted with dichloromethane, washed (water, brine), dried (Na2SO4), concentrated to crude which was purified by SiO2 column chromatography (10-20% EtOAc in hexane) to pure mass (0.64 g, 71%).

Workup

  1. customto attain 30° C.
  2. stirringstirring
  3. extractionThe organic layer was extracted with dichloromethane
  4. washwashed (water, brine)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to crude which
  7. customwas purified by SiO2 column chromatography (10-20% EtOAc in hexane) to pure mass (0.64 g, 71%)

Sources & evidence

ORD record
ord-02d7c436118c4fef9b7c95ff7269ca56
Source dataset
uspto-grants-2008_04
Patent number
US07355055B2

Reaction notes

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