Sodium Hydroxide → HCID 52949921, compound

HRID 854925Notes

Reaction equation

HRID 854925 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH:8]([C:13]([F:16])([F:15])[F:14])[C:7]([C:17]([O:19]CC)=[O:18])=[CH:6]2)[CH3:2].C1COCC1.CCO.O.[OH-].[Na+]>O>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH:8]([C:13]([F:14])([F:15])[F:16])[C:7]([C:17]([OH:19])=[O:18])=[CH:6]2)[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18504229Ethanol tetrahydrofuran waterHCID 69517042HCID 69517042, compound

Product 1

HCID 52949921HCID 52949921, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 15 mL single-neck round bottom flask was charged with ethyl 6-ethyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate (0.238 g, 0.932 mmole), THF:EtOH:H2O (7:2:1 by volume, 3 mL), and aqueous NaOH (0.41 mL of 2.5 N aq solution, 1.026 mmole). The reaction was stirred at RT under nitrogen for 3 days and was concentrated in vacuo (high vacuum) to yield a semi-solid. The semi-solid was dissolved in H2O, washed with diethyl ether, and sparged with nitrogen with gentle warming. The resulting organic solvent-free aqueous phase was acidified with concentrated HCl with stirring providing a slurry. The slurry was vacuum filtered yielding a white solid. The solid was dried on high vacuum yielding the title compound as a white powder (0.178 g, 70%): mp 145-149° C. LCMS m/z 273.15 (M+H). HRMS m/z 271.0600 (M−H, C13H10F3O, Cald'd 271.0577). 1H NMR (acetone-d6/300 MHz) 7.86 (s, 1H), 7.30 (d, 1H, J=2.0 Hz), 7.27 (d, 1H, J=8.3 Hz), 6.94 (d, 1H, J=8.3 Hz), 5.77 (q, 1H, J=7.0 Hz), 2.61 (q, 2H, J=7.5 Hz), 1.21 (t, 3H, J=7.5 Hz).

Workup

  1. concentrationwas concentrated in vacuo (high vacuum)
  2. customto yield a semi-solid
  3. washwashed with diethyl ether
  4. customsparged with nitrogen with gentle warming
  5. stirringwith stirring
  6. customproviding a slurry
  7. filtrationfiltered
  8. customyielding a white solid
  9. customThe solid was dried on high vacuum

Sources & evidence

ORD record
ord-c17884f297ec4d728c87092a72049750
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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