Ethanol → HCID 11473357, compound

HRID 854904Notes

Reaction equation

HRID 854904 reaction equation
[Cl:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([Cl:14])=[C:8]2[C:3]=1[CH:4]=[C:5]([C:19]([O:21]CC)=[O:20])[CH:6]([C:15]([F:18])([F:17])[F:16])[O:7]2.C1COCC1.CCO.O[Li].O>O>[Cl:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([Cl:14])=[C:8]2[C:3]=1[CH:4]=[C:5]([C:19]([OH:21])=[O:20])[CH:6]([C:15]([F:17])([F:18])[F:16])[O:7]2

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 69518339HCID 69518339, compound

Product 1

HCID 11473357HCID 11473357, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of the ester from Step 1 (0.174 g, 0.469 mmole) in a 7:2:1 THF:EtOH:H2O mixture (10 mL) was added LiOH.H2O (29.5 mg (0.704 mmole). The mixture was stirred at room temperature overnight and the solvent was removed in vacuo. The residue was redissolved in H2O, filtered (0.45 □ PTFE) and acidified with 1 N HCl. The resulting solid was filtered, washed with H2O and dried in vacuo to give 134 mg (83% yield) of the product as an yellow solid: ESHRMS m/z 340.9607 (M−H, C12H6C12F3O4, Calc'd 340.9590). 1H NMR (dmso-d6, 300 MHz) 13.70 (brs, 1H), 7.90 (s, 1H), 7.41 (s, 1H), 6.10 (q, 1H, J=7.1 Hz), 3.86 (s, 3H).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was redissolved in H2O
  3. filtrationfiltered (0.45 □ PTFE)
  4. filtrationThe resulting solid was filtered
  5. washwashed with H2O
  6. customdried in vacuo

Sources & evidence

ORD record
ord-1aed7ecca85c4b679b7371f873d12fa0
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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