Trifluoroacetic acid → 6-Phenethyl-dihydro-pyran-2,4-dione

HRID 1839865Notes

Reaction equation

HRID 1839865 reaction equation
C([O:5][C:6](=[O:21])[CH2:7][C:8](=[O:20])[CH2:9][CH:10](O)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:11]([CH:10]1[O:21][C:6](=[O:5])[CH2:7][C:8](=[O:20])[CH2:9]1)[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 695267015-Hydroxy-3-oxo-7-phenyl-heptanoic acid tert-butyl ester

Product 1

HCID 695272756-Phenethyl-dihydro-pyran-2,4-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-hydroxy-3-oxo-7-phenyl-heptanoic acid tert-butyl ester (0.96 g, 3.3 mmol) and TFA (0.38 g, 3.3 mmol) in DCM (60 mL) was stirred at rt for 18 h. Removal of the volatile components under reduced pressure afforded the product 6-Phenethyl-dihydro-pyran-2,4-dione as an off white solid (0.56 g, 78%). 1H NMR (300 MHz, CDCl3) δ1.9-2.2 (m, 2H), 2.4-2.7 (m, 2H), 2.75-2.95 (m, 2 H), 3.5 (q, 2H), 4.55-4.65(m, 1H), 7.10-7.35 (m, 5H). ESMS calcd (C13H14O3): 218.1; found: 219.1 (M+H)+.

Workup

  1. customRemoval of the volatile components under reduced pressure

Sources & evidence

ORD record
ord-192edaad9d7846aea597bdbd1b83dc65
Source dataset
uspto-grants-2004_01
Patent number
US06677462B2

Reaction notes

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