Ethyl Acetate → HCID 22056791, compound

HRID 1828643Notes

Reaction equation

HRID 1828643 reaction equation
C(OC([C:8]1[S:12][C:11]2[CH:13]=[CH:14][C:15]([O:17][CH2:18][C:19]([O:21]CC)=[O:20])=[CH:16][C:10]=2[C:9]=1[O:24]C(=O)C(C)(C)C)=O)CCC.[OH-].[Na+].C(OCC)(=O)C>C(O)(=O)C>[C:19]([CH2:18][O:17][C:15]1[CH:14]=[CH:13][C:11]2[S:12][CH:8]=[C:9]([OH:24])[C:10]=2[CH:16]=1)([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21028576HCID 21028576, compound

Product 1

HCID 22056791HCID 22056791, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.96 g (4.5 mmol) VIII and 2.70 g (67.5 mmol) NaOH were heated under reflux for 15 h in 300 ml degassed water. The pH was then adjusted to pH 1 with concentrated HCl and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over Na2SO4. Flash chromatography (200 g SiO2, ethyl acetate:acetic acid=100:1, pre-adsorption: 10 g SiO2/ethanol) yielded 801 mg (3.6 mmol, 79%) IX.

Workup

  1. temperatureunder reflux for 15 h in 300 ml
  2. customdegassed water
  3. extractionthe aqueous phase was extracted three times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over Na2SO4

Sources & evidence

ORD record
ord-5d481787e0274843ba69256079aeee8e
Source dataset
uspto-grants-2006_06
Patent number
US07060109B2

Reaction notes

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