Hydrochloric Acid → HCID 53638824, compound

HRID 2214852Notes

Reaction equation

HRID 2214852 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH2:4][O:5][C:6]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:7]=2[C:8]=1[C:9]([O:11]CC)=[O:10].[OH-].[Na+].Cl>C(O)C.O1CCCC1>[F:23][C:2]([F:1])([F:22])[C:3]1[CH2:4][O:5][C:6]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:7]=2[C:8]=1[C:9]([OH:11])=[O:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69662645HCID 69662645, compound

Product 1

HCID 53638824HCID 53638824, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the ester from Step 1 (0.8 g, 2.5 mmol) was dissolved in 40 mL of ethanol and 10 mL of tetrahydrofuran, treated with sodium hydroxide (2.5 N, 10 mL, 25 mmol) and stirred at room temperature for 16 hours. The reaction mixture was acidified with 1.0 N HCl, whereupon a solid formed that was isolated by filtration. The solid was washed with 20 mL of water to afford 0.7 g (95%) of the title compound as a yellow solid: mp 245.9–248.6° C. 1H NMR (acetone-d6/300 MHz) 8.57 (s, 1H), 8.28 (d, 1H, J=8.7 Hz), 8.03 (d, 1H, J=9.0 Hz), 7.93 (d, 1H, J=8.7), 7.67 (m, 1H), 7.50 (m, 1H), 7.28 (d, 1H, J=9.0), 5.96 (qH-F, 1H, J=7.2 Hz). FABHRMS m/z 295.0561 (M+H, Calc'd 295.0582). Anal. Calc'd for C15H9O3F3+3.31% H2O: C, 59.21; H, 3.35. Found: C, 59.17; H, 3.07.

Workup

  1. customformed that
  2. customwas isolated by filtration
  3. washThe solid was washed with 20 mL of water

Sources & evidence

ORD record
ord-8dafc45603304845b0fc4e4b8c86318f
Source dataset
uspto-grants-2006_09
Patent number
US07109211B2

Reaction notes

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