Methanol → HCID 57535890, compound

HRID 2358524Notes

Reaction equation

HRID 2358524 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][C:25]([CH2:33][O:34][CH2:35][O:36][CH3:37])([CH2:30][C:31]#[CH:32])[C:26]([O:28]C)=[O:27])=[C:18]([Cl:38])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.C1COCC1.[OH-].[Na+]>O.Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][C:25]([CH2:33][O:34][CH2:35][O:36][CH3:37])([CH2:30][C:31]#[CH:32])[C:26]([OH:28])=[O:27])=[C:18]([Cl:38])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57535889HCID 57535889, compound

Product 1

HCID 57535890HCID 57535890, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

The compound of Example 214 (1.129) was dissolved in a mixed solvent composed of MeOH:THF=1:1 (12 mL). To this solution, a 10% aqueous solution of sodium hydroxide (4 mL) was added and the mixture was refluxed. After 20 hours, the mixture was diluted with water, and hydrochloric acid was added to make the mixture acidic. The mixture was then extracted with ethyl acetate and the extract was washed with a saturated aqueous solution of sodium chloride. The organic phase was then dried over anhydrous magnesium sulfate. The solvent was removed to give the desired product as a yellow oil (1.09 g).

Workup

  1. temperaturethe mixture was refluxed
  2. additionwas added
  3. extractionThe mixture was then extracted with ethyl acetate
  4. washthe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialThe organic phase was then dried over anhydrous magnesium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-3070b113b37c442386ed1b468efb3a4b
Source dataset
uspto-grants-2010_07
Patent number
US07763752B2

Reaction notes

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