Benzyl Alcohol → HCID 57182103, compound

HRID 263689Notes

Reaction equation

HRID 263689 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 was dissolved in 88 ml of acetone, and 6.5 g of 1,1'-dicyclohexylcarbodiimide was added thereto, followed by stirring at room temperature for 2 hours. 3.26 ml of benzyl alcohol was added to the reaction solution, and stirred at the same temperature for 12 hours. Insoluble mattes were filtered off, and 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 7.93 g of the above-identified compound as yellow solid.

Workup

  1. stirringstirred at the same temperature for 12 hours
  2. filtrationInsoluble mattes 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-cff5903374734f129c7ccb69bdbd4f91
Source dataset
uspto-grants-1997_07
Patent number
US05643958

Reaction notes

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