Ethanol → HCID 58934612, compound

HRID 854898Notes

Reaction equation

HRID 854898 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:21][CH2:22][CH3:23])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18]CC)=[O:17])=[CH:7]2.C1COCC1.CCO.O[Li].O>O>[Cl:1][C:2]1[CH:3]=[C:4]([O:21][CH2:22][CH3:23])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([OH:18])=[O:17])=[CH:7]2

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 69519114HCID 69519114, compound

Product 1

HCID 58934612HCID 58934612, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of the ester from Step 4 (250 mg, 0.713 mmole) in a 7:2:1 THF:EtOH:H2O mixture (10 mL) was added LiOH.H2O (44.9 mg, 1.07 mmole). The mixture was stirred room temperature for 15 minutes and then at 50° C. for 75 minutes. After standing at room temperature for 2.75 days, the solvent was removed in vacuo. The residue was redissolved in H2O (20 mL) and washed with ethyl ether (20 mL). The aqueous layer was concentrated to a volume of 5 mL and acidified with 1 N HCl. The resulting solid was filtered, washed with H2O and dried in vacuo to give 216 mg (94% yield) of the product as a yellow crystalline solid: ESHRMS m/z 321.0135 (M−H, C13H9ClF3O4, Calc'd 321.0136). 1H NMR (dmso-d6/300 MHz) 13.45 (brs, 1H), 7.88 (s, 1H), 7.13-7.16 (m, 2H), 6.02 (q, 1H, J=7.3 Hz), 4.03 (q, 2H, J=6.9 Hz), 1.32 (t, 3H, J=6.9 Hz).

Workup

  1. waitat 50° C. for 75 minutes
  2. waitAfter standing at room temperature for 2.75 days
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was redissolved in H2O (20 mL)
  5. washwashed with ethyl ether (20 mL)
  6. concentrationThe aqueous layer was concentrated to a volume of 5 mL
  7. filtrationThe resulting solid was filtered
  8. washwashed with H2O
  9. customdried in vacuo

Sources & evidence

ORD record
ord-cdcfea8a650a4367968441385f80bed9
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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