Ethanol → HCID 70294261, compound

HRID 1107271Notes

Reaction equation

HRID 1107271 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14][CH:15]2[C:21]3[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=3[S:19][C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=3[CH2:16]2)[CH2:7]1)=[O:5])C.[OH-:31].[Na+].C([OH:35])C>>[C:4]([OH:3])(=[O:5])[C:6]([OH:35])=[O:31].[Cl:26][C:23]1[CH:24]=[CH:25][C:20]2[S:19][C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=3[CH2:16][CH:15]([O:14][CH2:13][CH2:12][N:8]3[CH2:9][CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7]3)[C:21]=2[CH:22]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 50851761HCID 50851761, compound

Product 1

HCID 70294261HCID 70294261, compoundYield 62%

Procedure

The above ester (5.4 g, 12.1 mmol) was dissolved in ethanol (50 ml), 5 N sodium hydroxide (5 ml) was added, and the mixture was stirred at room temperature for 20 h. Ethanol was evaporated in vacuo, water (50 ml) and acetic acid (7 ml) were added, and the mixture was extracted with dichloromethane (100 ml). The organic phase was dried (MgSO4) and the solvent was evaporated in vacuo. The residue was dissolved in acetone and treated with oxalic acid to give 3.8 g (62%) of the title compound.

Workup

  1. customEthanol was evaporated in vacuo, water (50 ml) and acetic acid (7 ml)
  2. additionwere added
  3. extractionthe mixture was extracted with dichloromethane (100 ml)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customthe solvent was evaporated in vacuo
  6. dissolutionThe residue was dissolved in acetone
  7. additiontreated with oxalic acid

Sources & evidence

ORD record
ord-3c784968e26b4ba8a03f32b78f7232e8
Source dataset
uspto-grants-2000_05
Patent number
US06060468

Reaction notes

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