Hydrochloric Acid → HCID 58934586, compound

HRID 855018Notes

Reaction equation

HRID 855018 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[O:9][CH:8]([C:14]([F:17])([F:16])[F:15])[C:7]([C:18]([O:20]CC)=[O:19])=[CH:6]2)[CH3:2].C(O)C.O.[OH-].[Li+].Cl>O>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[O:9][CH:8]([C:14]([F:15])([F:16])[F:17])[C:7]([C:18]([OH:20])=[O:19])=[CH:6]2)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 58934952HCID 58934952, compound

Product 1

HCID 58934586HCID 58934586, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To the product of step 2 was added 80 mL of ethanol, followed by addition of a solution of 3.5 g (83 mmol) of lithium hydroxide hydrate in 80 mL of water. The resulting solution was heated to reflux for three h. The mixture was concd, the residue treated with 50 mL of water and the resulting solution acidified to pH=1.0 with dilute hydrochloric acid. The product was extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over anhydrous magnesium sulfate. After removing the volatiles, the residue was further purified by silica chromatography with 1% HOAc in EtOAc/hexane (2:8) to afford 5.6 g (94%) of a green-yellow solid: 1H NMR (CDCl3/400 MHz) 7.80(s, 1H), 7.01(s, 1H), 6.43(s, 1H), 5.62(q, J=6.8Hz, 1H), 2.56(q, J=7.6 Hz, 2H), 1.26(t, J=7.6 Hz, 3H). MS (ESI+) 289.1(M+1, 100). MS(ES−) 287.1(M−H, 100). HRMS (ES−) m/z calcd for (M−H; C13H10F3O4): 287.0526, found 287.0504.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for three h
  3. extractionThe product was extracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removing the volatiles
  7. customthe residue was further purified by silica chromatography with 1% HOAc in EtOAc/hexane (2:8)

Sources & evidence

ORD record
ord-e473258e28c84c1984fd632a8d939017
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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