Sodium Hydroxide → HCID 13745939, compound

HRID 2290672Notes

Reaction equation

HRID 2290672 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][C:5]1[CH:30]=[CH:29][C:8]([O:9][CH2:10][C:11]2(O)[O:15][C:14]3[CH:16]=[CH:17][C:18]([C:21](=[O:23])[CH3:22])=[C:19]([OH:20])[C:13]=3[C:12]2([CH2:25][CH2:26][CH3:27])O)=[CH:7][CH:6]=1.[OH-].[Na+]>C1COCC1.O>[C:3]([CH2:4][C:5]1[CH:30]=[CH:29][C:8]([O:9][CH2:10][CH:11]2[O:15][C:14]3[CH:16]=[CH:17][C:18]([C:21](=[O:23])[CH3:22])=[C:19]([OH:20])[C:13]=3[CH:12]2[CH2:25][CH2:26][CH3:27])=[CH:7][CH:6]=1)([OH:31])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20231632HCID 20231632, compound

Product 1

HCID 13745939HCID 13745939, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound from Example 16 (650 mg, 1.63 moles) was taken up in 5 ml THF to which was added 1 N NaOH (4.2 ml). After three hours, the reaction volume wad diluted with H2O and the THF was removed in vacuo. The aqueous phase was wahsed with CHCl3, then acidified and extracted into CHCl3. The organic extract was dried and concentrated. The residue was triturated with ether to afford the title compound as a white solid which was recrystallized from toluene, m.p.: 104°-106°.

Workup

  1. customthe THF was removed in vacuo
  2. extractionextracted into CHCl3
  3. extractionThe organic extract
  4. customwas dried
  5. concentrationconcentrated
  6. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-71eb33a631124ceeab37c2498957d0fb
Source dataset
uspto-grants-1986_10
Patent number
US04617407

Reaction notes

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