2,5-Dimethyl-3(2H)-furanone → HCID 21875048, compound

HRID 723658Notes

Reaction equation

HRID 723658 reaction equation
[CH3:1][CH:2]1[C:6](=[O:7])[CH:5]=[C:4]([CH3:8])[O:3]1.[Si:9](OS(C(F)(F)F)(=O)=O)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]>C(Cl)Cl>[CH3:13][C:12]([Si:9]([CH3:11])([CH3:10])[O:7][C:6]1[CH:5]=[C:4]([CH3:8])[O:3][C:2]=1[CH3:1])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 857302,5-Dimethyl-3(2H)-furanoneHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonate

Product 1

HCID 21875048HCID 21875048, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,5-Dimethyl-3(3H)-furanone (2.00 g, 17.8 mmol) was dissolved in methylene chloride (180 mL). TEA (7.43 mL, 53.5 mmol) was added followed by TBSOTf (4.92 mL, 21.4 mmol) at 25° C. After 1 h, the reaction was concentrated in vacuo and the resulting slurry was run through a silica gel column conditioned with 3% TEA in hexanes. The product was eluted with 3% TEA/hexanes to give 3.6 g (89%) of compound 222A as an orange oil which was used directly in subsequent reactions.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. washThe product was eluted with 3% TEA/hexanes

Sources & evidence

ORD record
ord-6fa7125d47ad451d8e169eb9d24192a8
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Reaction notes

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