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

HRID 1004341

Reaction equation

HRID 1004341 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.[CH2:13](O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC(C)=O>[CH2:13]([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:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 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

5.2 g of (2RS,3SR)-5-oxotetrahydrofuran-2,3-dicarboxylic acid in 88 ml of acetone was stirred with 6.5 g of 1,1'-dicyclohexylcarboriimide at room temperature for 2 hours. After addition of 3.26 ml of benzyl alcohol, the reaction solution was stirred at the same temperature for 12 hours. The insolubles were filtered off, and the filtrated was concentrated under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=4/1→chloroform/methanol=50/1] to give 7.93 g of the title compound as a yellow solid.

Workup

  1. filtrationThe insolubles were filtered off
  2. concentrationthe filtrated was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=4/1→chloroform/methanol=50/1]

Sources & evidence

ORD record
ord-53bae2eb2847477aa7edbeafdcd3ac82
Source dataset
uspto-grants-2000_04
Patent number
US06048894

Linked notes

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