Ethyl Acetate → HCID 86731831, compound

HRID 1746349Notes

Reaction equation

HRID 1746349 reaction equation
[CH3:1][O:2][CH2:3][O:4][C@H:5]1[C@H:11]2[C@H:9]([O:10]2)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:6]1.CC[O:18]C(C)=O>C1COCC1.O.OS(O)(=O)=O>[OH:18][CH:9]1[C@H:11]([OH:10])[C@H:5]([O:4][CH2:3][O:2][CH3:1])[CH2:6][C:7]([C:12]([O:14][CH3:15])=[O:13])=[CH:8]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 57523006HCID 57523006, compound

Product 1

HCID 86731831HCID 86731831, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

To a well stirred solution of compound 14 (107 mg, 0.5 mmol) in THF/H2O (3:1), concentrated H2SO4 (5 drops) was added. The reaction was stirred for 2 h at 25° C. After the completion of reaction (monitored by TLC), the reaction mixture was diluted with excess of EtOAc 20 mL The organic layer is further washed with H2O, brine, dried over anhydrous Na2SO4. Removal of solvent under reduced pressure gave crude product which on chromatographic purification with petroleum ether/ethyl acetate (2:8 v/v) gave title compound 19 as gum.

Workup

  1. customAfter the completion of reaction (monitored by TLC)
  2. washis further washed with H2O, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customRemoval of solvent under reduced pressure
  5. customgave crude product which
  6. customon chromatographic purification with petroleum ether/ethyl acetate (2:8 v/v)

Sources & evidence

ORD record
ord-6b3cf5c975fc48f694b29056f0d2ed72
Source dataset
uspto-grants-2015_10
Patent number
US09150498B2

Reaction notes

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