Sodium Hydroxide → HCID 12018480, compound

HRID 650154Notes

Reaction equation

HRID 650154 reaction equation
[OH-].[Na+].[F:3][CH:4]([F:24])[C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH:12]([C:14]([F:17])([F:16])[F:15])[C:11]([C:18]([O:20]CC)=[O:19])=[CH:10][C:9]=2[CH:23]=1>C1COCC1.CCO.O>[F:24][CH:4]([F:3])[C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH:12]([C:14]([F:17])([F:15])[F:16])[C:11]([C:18]([OH:20])=[O:19])=[CH:10][C:9]=2[CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21883689HCID 21883689, compound

Product 1

HCID 12018480HCID 12018480, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

Aqueous NaOH (1.31 mL, 3.277 mmol, 2.5 M solution) was added in one portion to the ester (Step 1) (0.880 g, 2.731 mmol) in THF:EtOH:H2O (7:2:1, 10 mL). The resulting solution was stirred for 60 hours. The reaction mixture was partially concentrated in vacuo to remove the organic solvents and was diluted with H2O. The resulting aqueous solution was washed with diethyl ether, sparged with nitrogen to remove trace ether, and acidified with concentrated HCl. The resulting oily suspension was extracted with diethyl ether. The combined organic phases were dried over MgSO4, filtered and concentrated in vacuo yielding the title compound (0.483 g, 60%) as an oil which solidified as a white crystalline mass: mp 134.7-136.2° C. 1H NMR (acetone-d6/300 MHz) 7.97 (s, 1H), 7.73 (s, 1H), 7.67 (dd, 1H, J=8.5, 1.0 Hz), 7.17 (d, 1H, J=8.5 Hz), 6.89(t, 1H, J=56.2 Hz), 5.90 (q, 1H, J=7.1 Hz). FAB-ESLRMS m/z 293 (M−H). EIHRMS m/z 293.0235 (M−H, Calc'd 293.0237). Anal. Calc'd for C12H7F503: C, 49.00; H, 2.40. Found: C, 48.78; H, 2.21.

Workup

  1. concentrationThe reaction mixture was partially concentrated in vacuo
  2. customto remove the organic solvents
  3. additionwas diluted with H2O
  4. washThe resulting aqueous solution was washed with diethyl ether
  5. customsparged with nitrogen
  6. customto remove trace ether
  7. extractionThe resulting oily suspension was extracted with diethyl ether
  8. dry with materialThe combined organic phases were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf5e1728229e4392b0db8a86c3c51d3d
Source dataset
uspto-grants-2001_08
Patent number
US06271253B1

Reaction notes

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