Water → HCID 9899188, compound

HRID 1828649Notes

Reaction equation

HRID 1828649 reaction equation
C([O:3][C:4]([CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:11]2[O:12][CH2:13][C:14](=[O:15])[C:10]=2[CH:9]=1)=[O:5])C.O.OS(O)(=O)=O.[Na+].[Cl-]>O1CCCC1.C(O)C.C(O)(=O)C.C(OCC)(=O)C.CCCCCC>[C:4]([CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:11]2[O:12][CH2:13][C:14](=[O:15])[C:10]=2[CH:9]=1)([OH:5])=[O:3]

Participants

10

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 17937805HCID 17937805, compound

Product 1

HCID 9899188HCID 9899188, compoundYield 67%

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

4.72 g (20 mmol) XIX were heated under reflux for 15 h in a mixture of 200 ml tetrahydrofuran, 100 ml water and 10 ml concentrated H2SO4. Ethyl acetate and saturated NaCl solution were added to the reaction solution. The phases were separated and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over Na2SO4 and freed from the solvent. Flash chromatography (200 g SiO2, n-hexane:ethyl acetate=1:2+1% acetic acid, applied with ethanol) produced 2.78 g (13 mmol, 67%) XX.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over Na2SO4

Sources & evidence

ORD record
ord-36e93e22581b471181ffd183c012d407
Source dataset
uspto-grants-2006_06
Patent number
US07060109B2

Reaction notes

Loading…