Acetic Anhydride → (+)-Acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester

HRID 2558

Reaction equation

HRID 2558 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]1[CH2:12][C@H:11]([OH:13])[CH:10]=[CH:9]1.[C:14](OC(=O)C)(=[O:16])[CH3:15].CN(C1C=CC=CN=1)C.C(OCC)(=O)C>N1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]1[CH2:12][C@H:11]([O:13][C:14](=[O:16])[CH3:15])[CH:10]=[CH:9]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 218852-DimethylaminopyridineHCID 13623252cis-4-Tetrahydropyranyloxy 2-cyclopentenol

Product 1

HCID 13623284(+)-Acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dissolve (-)-cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enol (292 mg, 1.59 mmol, prepared in example 11) in pyridine (2.8 mL) and treat with acetic anhydride (0.39 mL) and dimethylaminopyridine (16 mg). Stir the reaction overnight. Concentrate the reaction under vacuum, dissolve the residue with ethyl acetate (10 mL). Wash with 0.5M hydrochloric acid that is 1/2 saturated with brine (2×10 mL), saturated sodium bicarbonate (10 mL), brine (10 mL), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by chromatography (silica gel, 10 g, 1.5×4 cm columnar 20% ethyl acetate/hexane) to provide the title compound (290 mg, 81%).

Workup

  1. customthe reaction overnight
  2. concentrationConcentrate
  3. customthe reaction under vacuum
  4. washWash with 0.5M hydrochloric acid that
  5. dry with materialdry over anhydrous magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customPurify the residue by chromatography (silica gel, 10 g, 1.5×4 cm columnar 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-00533d2621284180b8d6e372c9496cb7
Source dataset
uspto-grants-1998_03
Patent number
US05728899

Linked notes

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