Lithium hydroxide, monohydrate → 183500-60-9

HRID 1956683Notes

Reaction equation

HRID 1956683 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:15][C:16]#[C:17][CH3:18])[C:10]([O:12]CC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:15][C:16]#[C:17][CH3:18])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21187429HCID 21187429, compound

Product 1

HCID 21187433183500-60-9Yield 89.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the product from Step H (ca. 51.8 mmol) in THF (100 mL) and water (20 mL) was added at 0° C. a solution of lithium hydroxide monohydrate (6.5 g, 155 mmol). The solution was stirred for 1 hour at 0° C., then warmed to room temperature. After 48 hours, the solution was concentrated in vacuo. The aqueous mixture was extracted with EtOAc, acidified at 0° C. with 10% aq. HCl soln., then extracted with three portions of dichloromethane. The combined dichloromethane extracts were dried (Na2SO4), filtered, and concentrated in vacuo to provide the titled product as an orange oil (10.58 g).

Workup

  1. temperaturewarmed to room temperature
  2. waitAfter 48 hours
  3. concentrationthe solution was concentrated in vacuo
  4. extractionThe aqueous mixture was extracted with EtOAc
  5. customacidified at 0° C. with 10% aq. HCl
  6. extraction, then extracted with three portions of dichloromethane
  7. dry with materialThe combined dichloromethane extracts were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cdaf33ded2c54f189d75c53602ad7e4e
Source dataset
uspto-grants-1998_07
Patent number
US05780492

Reaction notes

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