Hydrochloric Acid → HCID 9911419, compound

HRID 992511Notes

Reaction equation

HRID 992511 reaction equation
[CH2:1]([C:3]1([CH2:36]C)[CH2:12][CH:11]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[C:9]2[CH:8]=[C:7]([C:23]#[C:24][C:25]3[CH:35]=[CH:34][C:28]([C:29]([O:31]CC)=[O:30])=[CH:27][CH:26]=3)[CH:6]=[CH:5][C:4]1=2)C.[OH-].[Na+].Cl>CCO.C1COCC1>[CH3:1][C:3]1([CH3:36])[CH2:12][CH:11]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:15][CH:14]=2)[C:9]2[CH:8]=[C:7]([C:23]#[C:24][C:25]3[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:34][CH:35]=3)[CH:6]=[CH:5][C:4]1=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18412269HCID 18412269, compound2×

Product 1

HCID 9911419HCID 9911419, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 4-[(5,6-dihydro-5,5 diethyl-8-(4-trifluoromethylphenyl)-2-naphthalenyl)ethynyl]benzoate (Compound 9) 70.0 mg (0.148 mmol) in 3 ml of EtOH and 2 ml of THF was added 60.0 mg (1.50 mmol, 1.50 ml) of NaOH (1.0 M aqueous solution). The solution was heated to 50° C. for 2 hours, cooled to room temperature, and acidified with 10% HCl. Extraction with EtOAc, followed by drying over Na2SO4, and removal of the solvents under reduced pressure afforded the title compound as a colorless solid. 1H NMR (DMSO): δ7.90 (2H, d, J=8.3 Hz), 7.80 (2H, d, J=8.1 Hz), 7.61-7.47 (6H, m), 6.97 (2H, s), 6.16 (1H, t, J=4.5 Hz), 2.37 (2H, d, J=4.6 Hz), 1.30 (6H, s).

Workup

  1. temperaturecooled to room temperature
  2. extractionExtraction with EtOAc
  3. dry with materialby drying over Na2SO4, and removal of the solvents under reduced pressure

Sources & evidence

ORD record
ord-430939e00b27480e89a0a163e1b22bb0
Source dataset
uspto-grants-2002_10
Patent number
US06469028B1

Reaction notes

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