Trifluoroacetic acid methylene chloride → HCID 18467927, compound

HRID 2229487Notes

Reaction equation

HRID 2229487 reaction equation
[CH3:1][C:2]1([C:8]([O:10]C(C)(C)C)=[O:9])[C:6](=[O:7])[CH2:5][CH2:4][O:3]1.F[C:16](F)(F)C(O)=O.ClCCl>>[CH3:1][C:2]1([C:8]([OH:10])=[O:9])[C:6](=[O:7])[CH2:5][CH:4]([CH3:16])[O:3]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86758360HCID 86758360, compound

Product 1

HCID 18467927HCID 18467927, compoundYield 68%

Procedure

2-Methyl-3-oxo-2-tetrahydrofuroic acid, t-butyl ester (100 mg, 0.5 mmol) was treated with 1/1 trifluoroacetic acid/dichloromethane at 0° C. The reaction mixture was stirred at room temperature until all starting material had disappeared by TLC. The excess trifluoroacetic acid was removed via a stream of nitrogen and the residue was coevaporated with dichloromethane and purified via a silica gel SepPak plug. This 30 provided 49 mg of the desired product (68%), homogeneous by TLC (Rf=0.1 in 4/1 hexane/ethyl acetate).

Workup

  1. customThe excess trifluoroacetic acid was removed via a stream of nitrogen
  2. custompurified via a silica gel SepPak plug

Sources & evidence

ORD record
ord-79c2649340124619ac8c72fd75ba8aae
Source dataset
uspto-grants-2002_07
Patent number
US06420418B1

Reaction notes

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