Trifluoroacetic acid → 2-tert-butyl-4H-pyran-4-one

HRID 874066Notes

Reaction equation

HRID 874066 reaction equation
O[C:2]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:3][C:4](=[O:9])[CH:5]=[CH:6][O:7]C.C(O)(C(F)(F)F)=O>C1C=CC=CC=1>[C:10]([C:2]1[O:7][CH:6]=[CH:5][C:4](=[O:9])[CH:3]=1)([CH3:11])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178495557HCID 178495557, compound

Product 1

HCID 592936742-tert-butyl-4H-pyran-4-oneYield 102.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5-hydroxy-1-methoxy-6,6-dimethyl-hepta-1,4-dien-3-one (Step 1.7) (6.8 g, 36.9 mmol) and TFA (5.65 mL, 74 mmol, 2 eq) in benzene (250 mL) is stirred for 14 h at rt and concentrated. Purification of the residue by silica gel column chromatography (Hex/EtOAc, 1:0→75:25) provides 5.74 g of the title compound as a yellow oil: ESI-MS: 153.1 [M+H]+; tR=3.21 min (System 1); TLC: Rf=0.22 (Hex/EtOAc, 1:1).

Workup

  1. concentrationconcentrated
  2. customPurification of the residue by silica gel column chromatography (Hex/EtOAc, 1:0→75:25)

Sources & evidence

ORD record
ord-644a96d6c7fc4bb1aaeeca0dd4e02433
Source dataset
uspto-grants-2015_03
Patent number
US08980259B2

Reaction notes

Loading…