Trifluoroacetic acid → 2-(1-Methylcyclopropyl)-4H-pyran-4-one

HRID 2066785Notes

Reaction equation

HRID 2066785 reaction equation
O/[C:2](/[C:10]1([CH3:13])[CH2:12][CH2:11]1)=[CH:3]\[C:4](=[O:9])/[CH:5]=[CH:6]/[O:7]C.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[CH3:13][C:10]1([C:2]2[O:7][CH:6]=[CH:5][C:4](=[O:9])[CH:3]=2)[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178495555HCID 178495555, compound

Product 1

HCID 574170892-(1-Methylcyclopropyl)-4H-pyran-4-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of (1Z,4E)-1-hydroxy-5-methoxy-1-(1-methyl-cyclopropyl)-penta-1,4-dien-3-one one (Step 1.7) (111 mmol) and TFA (221 mmol) in toluene (175 mL) was stirred for 15.5 h at rt and then concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a white solid. LC-MS: tR=1.48 min, [M+H]+ 151; TLC: Rf=0.26 (EtOAc).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified

Sources & evidence

ORD record
ord-e997e3ac78bd4423a715c08ce89eae04
Source dataset
uspto-grants-2012_10
Patent number
US08293753B2

Reaction notes

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