Hydrochloric Acid → HCID 58934506, compound

HRID 855016Notes

Reaction equation

HRID 855016 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:17]([O:19]CC)=[O:18])[CH:9]([C:13]([F:16])([F:15])[F:14])[O:10]2)=[CH:5][C:4]=1[CH:22]=[CH2:23].[OH-].[Li+].C(O)C.Cl>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:17]([OH:19])=[O:18])[CH:9]([C:13]([F:15])([F:16])[F:14])[O:10]2)=[CH:5][C:4]=1[CH:22]=[CH2:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3939Lithium HydroxideHCID 69516446HCID 69516446, compound

Product 1

HCID 58934506HCID 58934506, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

The isolated intermediate from step 1 (150 mg, 0.46 mmol) was dissolved in 3 mL of THF. To the resulting solution was added a solution of lithium hydroxide (2.3 mmol.) in 3 mL of water. To the resulting mixture was added 3 mL of ethanol. The resulting solution was heated to 80° C. for three h. The mixture was concd in vacuo and the residue acidified to pH=1.0 with dilute aqueous hydrochloric acid. The product was extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over anhydrous magnesium sulfate. The solution was concd in vacuo to afford 110 mg (52%) of the final product: 1H NMR (CDCl3/300 MHz) 7.80(s, 1H), 7.48(s, 1H), 6.98-6.88(dd, J=17.7 Hz, 11.2 Hz, 1H), 6.66(s, 1H), 5.80-5.69(m, 2H), 5.20(d, J=11.4 Hz, 1H), 3.90(s, 3H). MS (ESI+) 301.1 (M+1, 100). MS(ES−) 299.1 (M−H, 100). HRMS (ES−) m/z calcd for (C14H10F3O4) M−H: 299.0526, found 299.0500.

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-1007b418fd584aec839020eb4d92be69
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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