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

HRID 1430149Notes

Reaction equation

HRID 1430149 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 178495556HCID 178495556, compound

Product 1

HCID 574170892-(1-Methylcyclopropyl)-4H-pyran-4-oneYield 49.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-hydroxy-5-methoxy-1-(1-methyl-cyclopropyl)-penta-1,4-dien-3-one (Step 40.7) (1.07 g, 5.9 mmol) and TFA (0.9 mL, 11.7 mmol, 2 eq) in toluene (50 mL) is stirred for 14 h at rt and concentrated. Purification of the residue by silica gel column chromatography (Hex/EtOAc, 1:0→3:7) provides 442 mg of the title compound as a red solid: ESI-MS: 151.1 [M+H]+; tR=2.89 min (System 1); TLC: Rf=0.19 (Hex/EtOAc, 1:1).

Workup

  1. concentrationconcentrated
  2. customPurification of the residue by silica gel column chromatography (Hex/EtOAc, 1:0→3:7)

Sources & evidence

ORD record
ord-61b4b9e82e5645efa4d0b790d407c259
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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