Lithium hydroxide, monohydrate → HCID 89560111, compound

HRID 590413Notes

Reaction equation

HRID 590413 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=1)C.O.[OH-].[Li+]>C1COCC1>[O:16]=[C:14]([CH3:15])[CH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:17])=[O:3])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 115493804HCID 115493804, compound2×

Product 1

HCID 89560111HCID 89560111, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl[4-(2-oxopropyl)phenoxy]acetate (Intermediate 110, 786 mg, 3.33 mmol) in THF (24 mL) water was added (12 mL) and the mixture was stirred for 10 min. Then, lithium hydroxide monohydrate (420 mg, 10.01 mmol) was added and stirring was continued for 3.5 hours at room temperature. THF was evaporated from the reaction mixture and water was added (25 mL). The solution was acidified with 5N HCl until pH 2 was reached and the aqueous phase was extracted with CH2Cl2 (3×30 mL). The resulting organic extract was washed with water and brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to give the title compound (392 mg, 57% yield).

Workup

  1. stirringstirring
  2. waitwas continued for 3.5 hours at room temperature
  3. customTHF was evaporated from the reaction mixture and water
  4. additionwas added (25 mL)
  5. extractionthe aqueous phase was extracted with CH2Cl2 (3×30 mL)
  6. extractionThe resulting organic extract
  7. washwas washed with water and brine
  8. dry with materialdried over anhydrous sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-abe5cea6dca0498995a8575ac7425590
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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