Hexane → HCID 59264773, compound

HRID 2097317Notes

Reaction equation

HRID 2097317 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-cf2e9e2d589e4be88b27203caf59ef86
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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