Lithium hydroxide, monohydrate → HCID 22323721, compound

HRID 324230Notes

Reaction equation

HRID 324230 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, compound

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- 12-(1,l-dimethyl-3-(4-methylphenyl3-5- 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-0963cf6354554046a943fd2d1de5e6ac
Source dataset
uspto-grants-2001_04
Patent number
US06218128B1

Reaction notes

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