Sodium Hydroxide → HCID 9905434, compound

HRID 722287Notes

Reaction equation

HRID 722287 reaction equation
[Cl:1][C:2]1[C:3]([CH3:22])=[C:4]([Cl:21])[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.C(O)C>[Cl:1][C:2]1[C:3]([CH3:22])=[C:4]([Cl:21])[C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([OH:17])=[O:16])=[CH:7][C:6]=2[CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21883645HCID 21883645, compound

Product 1

HCID 9905434HCID 9905434, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ester from Step 2 (8.39 g 23.6 mmol) was dissolved in THF (30 mL) and ethanol (20 mL), treated with 2.5 N sodium hydroxide (20 mL, 50 mmol), and stirred at room temperature for 3.5 hours. The reaction mixture was concentrated in vacuo, acidified with 3 N HCl, filtered, and recrystallized from ethanol/water to yield a yellow solid (6.0 g, 78%): mp 229.9–230.9° C. 1H NMR (acetone-d6/300 MHz) 7.90 (s, 1H), 7.58 (s, 1H), 6.00 (q, 1H, J=6.8 Hz), 2.50 (s, 3H). FABLRMS m/z 325 (M−H). FABHRMS m/z 324.9636 (M−H, Calc'd 324.9646). Anal. Calc'd for C12H7Cl2F3O3: C, 44.07; H, 2.16; Cl, 21.68. Found: C, 44.06; H, 2.21; Cl, 21.74.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationfiltered
  3. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-52e2c131f6594c0493cddced3f01c53f
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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