Sodium Hydroxide → HCID 21883628, compound

HRID 2214862Notes

Reaction equation

HRID 2214862 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[O:22])[C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17]CC)=[O:16])=[CH:7][C:6]=2[CH:20]=1.[OH-].[Na+]>C1COCC1.CCO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[O:22])[C:5]2[O:10][CH:9]([C:11]([F:13])([F:14])[F:12])[C:8]([C:15]([OH:17])=[O:16])=[CH:7][C:6]=2[CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21883599HCID 21883599, compound

Product 1

HCID 21883628HCID 21883628, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a stirred solution of the ester (Step 3)(0.284 g, 0.849 mmol) in THF:EtOH:H2O (7:2:1, 5 mL) was added aqueous NaOH solution (0.41 mL of 2.5 M, 1.02 mmol). After stirring 40 hours, the reaction was partially concentrated in vacuo to remove the organic solvents, diluted with H2O, washed with diethyl ether, sparged with nitrogen to remove trace diethyl ether, and acidified with concentrated HCl yielding a suspension. Vacuum filtration of the suspension yielded the title compound as a pale yellow powder (0.160 g, 23%). mp 243.3–252.4° C. 1H NMR (acetone-d6/300 MHz) 10.39 (s, 1H), 7.98 (s, 1H), 7.88 (d, 1H, J=2.6 Hz), 7.75 (d, 1H, J=2.6 Hz), 6.08 (q, 1H, J=6.9 Hz). FABLRMS m/z 307 (M+H). ESHRMS m/z 304.9839 (M−H, Calc'd 304.9828). Anal. Calc'd for C12H6Cl1F3O4: C, 47.01; H, 1.97. Found: C, 46.64; H, 1.86.

Workup

  1. concentrationthe reaction was partially concentrated in vacuo
  2. customto remove the organic solvents
  3. additiondiluted with H2O
  4. washwashed with diethyl ether
  5. customsparged with nitrogen
  6. customto remove trace diethyl ether
  7. filtrationVacuum filtration of the suspension

Sources & evidence

ORD record
ord-d24669c6c82a41979ffe8a04d0c53b27
Source dataset
uspto-grants-2006_09
Patent number
US07109211B2

Reaction notes

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