HCID 53666689, compound → HCID 54438093, compound

HRID 344828Notes

Reaction equation

HRID 344828 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[CH:10][CH:11]([OH:20])[CH2:12][CH:13]([OH:19])[CH2:14][C:15]([O:17][CH3:18])=[O:16]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[CH:10][C:11](=[O:20])[CH2:12][CH:13]([OH:19])[CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 1

HCID 53666689HCID 53666689, compound

Product 1

HCID 54438093HCID 54438093, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

Activated manganese dioxide (40 g) was added to a solution of methyl 7-(2,4-dichlorophenyl)-3,5-dihydroxy-6-heptenoate (6.8 g, 21.3 mmol) in chloroform (600 mL) and the black suspension was vigorously stirred at ambient temperature for 20 hours. After filtration and evaporation of the solvent the residual amber oil (4.5 g, 1 major spot on TLC with Rf 0.61 on Whatman MK6F silica using CHCl -MeOH; 19:1 as eluent) was chromatographed on a Still column to obtain the product (3.9 g, 58%) as a pale yellow oil which solidified on standing, m.p. 77°-79° C.; NMR (CDCl3) δ: 2.57 (2H, d, J=6Hz, --C2CO2 --), 2.93 (2H, d, J=6Hz, --CH2 --CO--), 3.70 (3H, s, --CO2CHp3), 4.4-4.8 (H, m, --CH(OH)--), 6.67 (H, d, J=16 Hz, =CH--CO), 7.1-7.7 (3H, m. ArH), 7.93 (H, d, J=16 Hz, =CH).

Workup

  1. filtrationAfter filtration and evaporation of the solvent the residual amber oil (4.5 g, 1 major spot on TLC with Rf 0.61 on Whatman MK6F silica using CHCl -MeOH; 19:1 as eluent)
  2. customwas chromatographed on a Still column

Sources & evidence

ORD record
ord-83f205a031f943ac99082787b3c3b077
Source dataset
uspto-grants-1991_10
Patent number
US05053525

Reaction notes

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