Benzyl Alcohol → (2RS,3SR)-2-benzyloxycarbonyl-5-oxotetrahydrofuran-3-carboxylic acid

HRID 850663

Reaction equation

HRID 850663 reaction equation
[O:1]=[C:2]1[O:6][CH:5]([C:7]([OH:9])=[O:8])[CH:4]([C:10]([OH:12])=[O:11])[CH2:3]1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:28](O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CC(C)=O>[CH2:28]([O:8][C:7]([CH:5]1[CH:4]([C:10]([OH:12])=[O:11])[CH2:3][C:2](=[O:1])[O:6]1)=[O:9])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 98259Tetrahydro-5-oxofuran-2,3-dicarboxylic acid

Product 1

HCID 18705291(2RS,3SR)-2-benzyloxycarbonyl-5-oxotetrahydrofuran-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.3 g of (2RS,3SR)-5-oxotetrahydrofuran-2,3-dicarboxylic acid was dissolved in 90 ml of acetone, and 6.6 g of N,N'-dicyclohexylcarbodiimide was added thereto, followed by stirring at room temperature for 2.5 hours. 3.3 ml of benzyl alcohol was added to the reaction solution, followed by stirring at the same temperature for 2 days. Insoluble matters were filtered off, and then the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→chloroform/methanol=50/1) to obtain 6.55 g of the above-identified compound as a yellow solid.

Workup

  1. stirringby stirring at the same temperature for 2 days
  2. filtrationInsoluble matters were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-cd627dccbfa1438d8ac7e20cb7de5762
Source dataset
uspto-grants-2000_01
Patent number
US06017956

Linked notes

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