Water → HCID 9964339, compound

HRID 1828652Notes

Reaction equation

HRID 1828652 reaction equation
C[O:2][C:3]1[C:4]2[CH:11]=[C:10]([O:12][CH2:13][CH2:14][O:15]C(=O)C)[CH:9]=[CH:8][C:5]=2[O:6][CH:7]=1.O.OS(O)(=O)=O.[Na+].[Cl-]>O1CCCC1.C(OCC)(=O)C>[OH:15][CH2:14][CH2:13][O:12][C:10]1[CH:9]=[CH:8][C:5]2[O:6][CH2:7][C:3](=[O:2])[C:4]=2[CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 17937804HCID 17937804, compound

Product 1

HCID 9964339HCID 9964339, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

751 mg (7.0 mmol) XXII were stirred under reflux for 12 h in a mixture of 40 ml tetrahydrofuran, 20 ml water and 0.5 ml conc. H2SO4. Ethyl acetate and saturated NaCl solution were added to the reaction mixture cooled to room temperature. After separation of the phases, the aqueous phase was extracted twice with ethyl acetate and the combined organic phases were dried over Na2SO4. After column filtration (50 g SiO2, n-hexane:ethyl acetate=1:1+1% acetic acid, applied with ethyl acetate), XXIII was obtained in a yield of 448 mg (2.3 mmol, 77%).

Workup

  1. customAfter separation of the phases
  2. extractionthe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialthe combined organic phases were dried over Na2SO4
  4. filtrationAfter column filtration (50 g SiO2, n-hexane:ethyl acetate=1:1+1% acetic acid, applied with ethyl acetate)

Sources & evidence

ORD record
ord-5220a8cda524421caa2c272de7d13be9
Source dataset
uspto-grants-2006_06
Patent number
US07060109B2

Reaction notes

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