Acetate → 1-(1-Hydroxyethyl)-3-oxocyclopentanecarboxylic acid

HRID 643542Notes

Reaction equation

HRID 643542 reaction equation
C([O:4][CH:5]([C:7]1([C:16]([O:18]C(C)(C)C)=[O:17])[CH2:11][CH2:10][C:9](OC)([O:12]C)[CH2:8]1)[CH3:6])(=O)C.C([O-])(=O)C>Cl.O1CCOCC1.O>[OH:4][CH:5]([C:7]1([C:16]([OH:18])=[O:17])[CH2:11][CH2:10][C:9](=[O:12])[CH2:8]1)[CH3:6]

Participants

6

Reactant 2

HCID 175AcetateHCID 68534118Tert-butyl 1-[1-(acetyloxy)ethyl]-3,3-dimethoxycyclopentanecarboxylate

Product 1

HCID 578805271-(1-Hydroxyethyl)-3-oxocyclopentanecarboxylic acid

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 1-[1-(acetyloxy)ethyl]-3,3-dimethoxycyclopentanecarboxylate (8.04 g, 25.4 mmol) was dissolved in anhydrous 4N HCl in dioxane (ca. 50 mL) and 5 mL of water was added (this was a mistake which led to inadvertent hydrolysis of the acetate). The reaction mixture was stirred at rt for 5 h, then was concentrated. Purification by flash chromatography (silica, 8% methanol/DCM) afforded 1-(1-hydroxyethyl)-3-oxocyclopentanecarboxylic acid.

Workup

  1. additionwas added (
  2. concentrationwas concentrated
  3. customPurification by flash chromatography (silica, 8% methanol/DCM)

Sources & evidence

ORD record
ord-edfccfa2496b431c9033abe2df2c684c
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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