Lithium Hydroxide → HCID 19034184, compound

HRID 265878Notes

Reaction equation

HRID 265878 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1COCC1.[Li+].[OH-]>CCOC(C)=O.OS([O-])(=O)=O.[K+]>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:26][CH:27]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 19034143HCID 19034143, compound

Product 1

HCID 19034184HCID 19034184, compoundYield 101.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516920Potassium bisulfateSolvent

Procedure

A mixture of 16-5 (0.75 g, 2 mmol), THF (30 ml) and 1N LiOH (10 mL) was heated at reflux for 7 h. The cooled reaction mixture was diluted with EtOAc and 10% KHSO4. The organic portion was then washed with brine, dried (MgSO4) and concentrated to give 16-6 (740 mg) as a white solid. Rf 0.86 (silica, EtOAc).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 h
  3. customThe cooled reaction mixture
  4. washThe organic portion was then washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-13907b7eeffd48fe9e052a2c79febdad
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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