Sodium Hydroxide → HCID 12018483, compound

HRID 722315Notes

Reaction equation

HRID 722315 reaction equation
[C:1]([C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH:16]([C:18]([F:21])([F:20])[F:19])[C:15]([C:22]([O:24]CC)=[O:23])=[CH:14][C:13]=2[CH:27]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.C(O)C>[C:1]([C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH:16]([C:18]([F:21])([F:20])[F:19])[C:15]([C:22]([OH:24])=[O:23])=[CH:14][C:13]=2[CH:27]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21883641HCID 21883641, compound

Product 1

HCID 12018483HCID 12018483, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ester from Step 1 (0.24 g, 0.64 mmol) was dissolved in THF (2 mL) and ethanol (2 mL), treated with 2.5 N sodium hydroxide (1.5 mL, 3.8 mmol), and stirred at room temperature for 4.3 hours. The reaction mixture was concentrated in vacuo, acidified with 3N HCl yielding a solid. The solid was collected by filtration and was recrystallized from ethanol-water to yield a white solid(0.14 g, 64%): mp 269.8–270.8° C. 1H NMR (acetone-d6/300 MHz) 8.04 (s, 1H), 7.99 (d, 1H, J=2.0 Hz), 7.88 (dd, 1H, J=8.5 Hz 2.0 Hz), 7.79 (m, 2H), 7.68 (m, 1H), 7.57 (m, 1H), 7.23 (d, 1H, J=8.6 Hz), 5.98 (q, 1H, J=7.0 Hz). FABLRMS m/z 347 (M−H). ESHRMS m/z 347.0560 (M−H, Calc'd 347.0531). Anal. Calc'd for C18H11F3O4: C, 62.08; H, 3.18. Found: C, 61.48; H, 3.22.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationThe solid was collected by filtration
  3. customwas recrystallized from ethanol-water

Sources & evidence

ORD record
ord-3e4625c8258e4dada747ec7fb9cb8aad
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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