Benzyl Alcohol → HCID 57182103, compound

HRID 2287497Notes

Reaction equation

HRID 2287497 reaction equation
[O:1]=[C:2]1[O:6][C@H:5]([C:7]([OH:9])=[O:8])[C@H: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]([C@@H:5]1[C@H: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 853429(-)-cis-Isocitric acid lactone

Product 1

HCID 57182103HCID 57182103, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.2 g of (2S,3R)-5-oxotetrahydrofuran-2,3-dicarboxylic acid in 88 ml of acetone was stirred with 6.5 g of 1,1'-dicyclohexylcarbodiimide at room temperature for 2 hours. 3.26 ml of benzyl alcohol was added, and the reaction solution was stirred at the same temperature for 12 hours. The insolubles were filtered off, the filtrate was concentrated in vacuo. 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 filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=4/1→chloroform/methanol=50/1]

Sources & evidence

ORD record
ord-43e48c8033f745c5b56a7958b8fd936b
Source dataset
uspto-grants-2000_07
Patent number
US06083985

Reaction notes

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