Lithium hydroxide, monohydrate → HCID 22323721, compound

HRID 1976660Notes

Reaction equation

HRID 1976660 reaction equation
[CH3:1][C:2]1([CH3:31])[C:10]2[C:5](=[CH:6][C:7]([C:11]#[C:12][C:13]3[CH:23]=[CH:22][C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][CH:14]=3)=[CH:8][CH:9]=2)[C:4]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)=[CH:3]1.O[Li].O>C1COCC1.O>[CH3:1][C:2]1([CH3:31])[C:10]2[C:5](=[CH:6][C:7]([C:11]#[C:12][C:13]3[CH:23]=[CH:22][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=3)=[CH:8][CH:9]=2)[C:4]([C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)=[CH:3]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22323723HCID 22323723, compound2×

Product 1

HCID 22323721HCID 22323721, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 10.0 mg (0.025 mmol) of ethyl 4- [2-(1,1-dimethyl-3-(4-methylphenyl)-5- indenyl)ethynyl]benzoate (Compound 47) in 0.5 ml THF/H2O (3:1 v/v) was added 5.2 mg (0.12 mmol) LiOH H2O. After stirring at room temperature for 48 hours the solution was extracted with hexanes and the aqueous layer was acidified with saturated aqueous NH4Cl. Solid NaCl was added and the resulting mixture extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to give the title compound as a colorless solid. 1H NMR (300 MHz, d6-DMSO): δ 7.95 (2H, d, J=8.3 Hz), 7.65 (2H, d, J 8.3 Hz), 7.57 (2H, m), 7.49 (3H, m), 7.30 (2H, d, J=7.9 Hz), 6.61 (1H, s), 2.36 (3H, s). 1.36 (6H, s).

Workup

  1. extractionwas extracted with hexanes
  2. additionSolid NaCl was added
  3. extractionthe resulting mixture extracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7fbf695c6f384c6bb36f1a82cdb23ae2
Source dataset
uspto-grants-2001_05
Patent number
US06228848B1

Reaction notes

Loading…