Diethyl Ether → 5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

HRID 1797432Notes

Reaction equation

HRID 1797432 reaction equation
C([O:4][CH:5]1[CH2:13][CH:8]2[O:9][C:10](=[O:12])[CH2:11][CH:7]2[CH:6]1[CH2:14][O:15]C(=O)C)(=O)C.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.C(OCC)C>CO>[OH:4][CH:5]1[CH2:13][CH:8]2[O:9][C:10](=[O:12])[CH2:11][CH:7]2[CH:6]1[CH2:14][OH:15]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 494700HCID 494700, compound

Product 1

HCID 37592585-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-oneYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 50 (10.0 g, 39 mmol) in MeOH (100 mL) was added potassium carbonate (15 g). The suspension was stirred at room temperature for 3 hours. To the suspension was added ethyl acetate (60 mL). The resulting suspension was filtered through a pad of diatomaceous earth (Celite®). The filtrate was concentrated in vacuo to give crude product. The crude product was dissolved in MeOH (15 mL) and to it was added diethyl ether (100 mL). The resulting suspension was stirred for 2 hours at room temperature. The solid was filtered to give the title compound (3.62 g, 54%).

Workup

  1. filtrationThe resulting suspension was filtered through a pad of diatomaceous earth (Celite®)
  2. concentrationThe filtrate was concentrated in vacuo
  3. customto give crude product
  4. stirringThe resulting suspension was stirred for 2 hours at room temperature
  5. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-6f34206cda2b405bb627a938751fc864
Source dataset
uspto-grants-2006_04
Patent number
US07034152B2

Reaction notes

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