Lithium Hydroxide → HCID 22619634, compound

HRID 840505Notes

Reaction equation

HRID 840505 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:29]=[CH:28][C:12]2[CH:13]([CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:14]3[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=3[CH2:16][CH2:17][C:11]=2[CH:10]=1)C.C1COCC1.[OH-].[Li+]>O.CO>[CH3:27][N:25]([CH3:26])[CH2:24][CH2:23][CH2:22][CH:13]1[C:12]2[CH:28]=[CH:29][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:30])=[O:3])=[CH:10][C:11]=2[CH2:17][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]1=2

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 69140908HCID 69140908, compound

Product 1

HCID 22619634HCID 22619634, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 875 mg of 7 (2.1 mmol) in 10 ml of freshly distilled THF was added a solution of 875 mg of lithium hydroxide in 10 ml of water and 5 ml of methanol. The reaction was allowed to stir at room temperature 18 hours and concentrated to remove THF and methanol. The aqueous residue was adjusted to pH 6 with 6N HCl. This was extracted with 3×100 ml of dichloromethane. The pH of the aqueous part was readjusted to 6 again after first extraction. The combined organic part was dried (Na2SO4) and concentrated to give 790 mg (2.0 mmol, 97%) of 8 as white amorphous solid.

Workup

  1. concentrationconcentrated
  2. customto remove THF and methanol
  3. extractionThis was extracted with 3×100 ml of dichloromethane
  4. extractionagain after first extraction
  5. dry with materialThe combined organic part was dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2d677938c1ff4ffbab2f24f81ff40142
Source dataset
uspto-grants-2002_04
Patent number
US06368814B1

Reaction notes

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