Citric Acid → (5S)-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-one

HRID 2209840Notes

Reaction equation

HRID 2209840 reaction equation
[OH:1][CH2:2][C@H:3]1[O:7][C:6](=[O:8])[CH2:5][CH2:4]1.N1C=CN=C1.Cl[Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[Si:15]([O:1][CH2:2][C@H:3]1[O:7][C:6](=[O:8])[CH2:5][CH2:4]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2733813(S)-(+)-gamma-Hydroxymethyl-gamma-butyrolactone

Product 1

HCID 10014094(5S)-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 13.2 g (113 mmol) of (5S)-dihydro-5-(hydroxymethyl)furan-2(3H)-one in 200 ml of dimethyiformamide was treated sequentially with 9.28 g (136 mmol) of imidazole and 18.84 g (125 mmol) of chloro-t-butyldimethylsilane, the latter in several portions. The resulting solution was stirred at ambient temperature for 6 h, poured into 10% aqueous citric acid, and extracted with ethyl acetate. The organic layer was washed sequentially with two portions of water, one portion of aqueous NaHCO3 and one portion of saturated brine. The organic layer was dried over MgSO4, and concentrated in vacuo to provide 22.04 g (90%) of the desired compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed sequentially with two portions of water, one portion of aqueous NaHCO3 and one portion of saturated brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e693f7ec1d94189802182bf08225e87
Source dataset
uspto-grants-1995_10
Patent number
US05455351

Reaction notes

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