Benzoate → HCID 12017640, compound

HRID 324206Notes

Reaction equation

HRID 324206 reaction equation
C([O-])(=O)C1C=CC=CC=1.[CH3:10][C:11]1([CH3:41])[CH2:20][CH:19]=[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=2)[C:17]2[CH:16]=[C:15]([C:28]#[C:29][C:30]3[CH:40]=[CH:39][C:33]([C:34]([O:36]CC)=[O:35])=[CH:32][CH:31]=3)[CH:14]=[CH:13][C:12]1=2.[OH-].[Na+].Cl>CCO.C1COCC1>[CH3:10][C:11]1([CH3:41])[CH2:20][CH:19]=[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=2)[C:17]2[CH:16]=[C:15]([C:28]#[C:29][C:30]3[CH:31]=[CH:32][C:33]([C:34]([OH:36])=[O:35])=[CH:39][CH:40]=3)[CH:14]=[CH:13][C:12]1=2

Participants

7

Reactant 4

HCID 242BenzoateHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15870720HCID 15870720, compound

Product 1

HCID 12017640HCID 12017640, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 4-1(5,6-dihydro-5,5-dimethyl-8-(3-methylphenyl)-2-naphthalenyl)ethynyl]benzoate (Compound 2) 30.0 mg (0.071 mmol) in 3 ml of EtOH and 2 ml of THF was added 28.0 mg (0.70 mmol, 0.7 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): δ 7.90 (2H, d, J=8.5 Hz), 7.59 (2H, d, J=8.5 Hz), 7.46 (2H, s), 7.32-7.13 (4H, m), 7.10 (1H, s), 6.98 (1H, t, J=4.5 Hz), 2.34 (3H, s), 2.31 (2H, d, J=4.5 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-1c19b33514274fb98238311e050f2077
Source dataset
uspto-grants-2001_04
Patent number
US06218128B1

Reaction notes

Loading…