Hexane → HCID 59264773, compound

HRID 646531Notes

Reaction equation

HRID 646531 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[C:5](=O)[CH:6]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:7]([C:9]1[CH:14]=[C:13]([CH2:15][CH3:16])[C:12]([OH:17])=[CH:11][C:10]=1[OH:18])=[O:8])[CH3:2].CCOC(C)=O.CCCCCC>Cl.CO>[CH2:1]([O:3][C:4]([C:5]1[O:18][C:10]2[C:9]([C:7](=[O:8])[C:6]=1[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[CH:14][C:13]([CH2:15][CH3:16])=[C:12]([OH:17])[CH:11]=2)=[O:27])[CH3:2]

Participants

6

Reactant 3

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 59264848HCID 59264848, compound

Product 1

HCID 59264773HCID 59264773, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

4-(5-Ethyl-2,4-dihydroxy-phenyl)-3-(4-fluoro-phenyl)-2,4-dioxo-butyric acid ethyl ester (3.22 g, 8.6 mmol) was refluxed in a mixture of 0.8M HCl and MeOH (20 ml/20 ml) for 3 hours at 100° C. After that, MeOH was evaporated and the aq. layer was extracted with EtOAc (2×60 ml). The combined organic layers were washed with sat. NaHCO3 (1×80 ml), brine (2×80 ml), water (1×80 ml) and dried with Na2SO4. After purification with decolourising charcoal and evaporation of the solvent, brown sticky solids were obtained. They were then extracted with hot ether, dark yellow solids were obtained (0.26 g). Rf=0.43 (EtOAc:n-hexane/1:2). LCMS: (M+1)+=357.3 (RT=7.83). 1H NMR (d6-acetone) δ=9.75 (1H, s); 7.80 (1H, s); 7.25 (2H, m); 7.10 (1H, m); 6.90 (1H, s); 4.05 (2H, q); 2.70 (2H, q); 1.20 (3H, t) and 0.95 (3H, t).

Workup

  1. customAfter that, MeOH was evaporated
  2. extractionthe aq. layer was extracted with EtOAc (2×60 ml)
  3. washThe combined organic layers were washed with sat. NaHCO3 (1×80 ml), brine (2×80 ml), water (1×80 ml)
  4. dry with materialdried with Na2SO4
  5. customAfter purification
  6. customwith decolourising charcoal and evaporation of the solvent
  7. custombrown sticky solids were obtained
  8. extractionThey were then extracted with hot ether
  9. customdark yellow solids were obtained (0.26 g)
  10. custom=357.3 (RT=7.83)

Sources & evidence

ORD record
ord-ad9ad18312da4abf9060bf41718a249e
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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