Water → HCID 15230861, compound

HRID 1646793Notes

Reaction equation

HRID 1646793 reaction equation
O.C[O:3][C:4]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[C:7]([O:14]C)=[C:6]([CH3:16])[C:5]=1[CH:17]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24]>C(#N)C>[CH3:13][O:12][C:8]1[C:7](=[O:14])[C:6]([CH3:16])=[C:5]([CH:17]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[C:4](=[O:3])[C:9]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 962WaterHCID 19088034HCID 19088034, compound

Product 1

HCID 15230861HCID 15230861, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solvent mixture of acetonitrile (12 ml) and water (6 ml) was added to 2.01 g (5.0 mmole) of 7-(2,3,4,5-tetramethoxy-6-methylphenyl)-7-phenylheptanol and 2.51 g (5×3 mmole) of 2,6-pyridinecarboxylic acid, and a cooled solution of 8.22 g (5×3 mmole) of ceric ammonium nitrate in 50% aqueous acetonitrile (16 ml) was added dropwise to the mixture over the 20 minutes period under ice-cooling. After stirring was continued for another 20 minutes under ice-cooling, the insoluble matter was filtered out, and the acetonitrile was distilled off under reduced pressure. Isopropyl ether was added to the residue to carry out extraction. The isopropyl ether layer was separated out, washed with aqeuous sodium chloride solution, dried (magnesium sulfate) and evaporated. The residue was chromatographed on a silica gel column to elute with isopropyl ether/ethyl acetate to give 1.56 g (84%) of 7-(5,6-dimethoxy-3-methyl-1,4-benzoquinon -2-yl)-7-phenylheptanol. Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 1. By following the procedure of this Example, the Compound No. 57 was prepared.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationthe insoluble matter was filtered out
  4. distillationthe acetonitrile was distilled off under reduced pressure
  5. additionIsopropyl ether was added to the residue
  6. extractionextraction
  7. customThe isopropyl ether layer was separated out
  8. washwashed with aqeuous sodium chloride solution
  9. dry with materialdried (magnesium sulfate)
  10. customevaporated
  11. customThe residue was chromatographed on a silica gel column
  12. washto elute with isopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-b7506b2a0077480a96871543023b5c84
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

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