Trifluoroacetic acid → HCID 24885562, compound

HRID 1839867Notes

Reaction equation

HRID 1839867 reaction equation
C([O:5][C:6](=[O:22])[CH2:7][C:8](=[O:21])[CH2:9][CH:10](O)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][CH2:11][CH:10]2[O:22][C:6](=[O:5])[CH2:7][C:8](=[O:21])[CH2:9]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69526798HCID 69526798, compound

Product 1

HCID 24885562HCID 24885562, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 7-(4-Fluoro-phenyl)-5-hydroxy-3-oxo-heptanoic acid tert-butyl ester (0.64 g, 2.06 mmol) in dry DCM was added TFA (0.24 g, 2.1 mmol) at 0° C. The resultant clear solution was stirred at rt for 16h. Removal of the volatile components under reduced pressure afforded the product 6-[2-(4-Fluoro-phenyl)-ethyl]-dihydro-pyran-2,4-dione as a white solid (0.32g, 66%). 1H NMR (300 MHz, CDCl3) δ1.8-2.2 (m, 2H), 2.25-2.55 (m, 2H), 2.65-2.95 (m, 2H), 3.55 (dd, ˜1H, J=10), 4.25-4.40(m, ˜0.5H), 4.6-4.7 (m, ˜0.5 H), 5.2 (s, ˜0.5 H), 6.90-7.05 (m, 2H), 7.1-7.2 (m, 2H), 10.8 (br, ˜0.5H). ESMS calcd (C13H13FO3): 236.1; found: 237.1 (M+H)+.

Workup

  1. customRemoval of the volatile components under reduced pressure

Sources & evidence

ORD record
ord-b7fd0b11ffbf403d9f66aae80fc087e1
Source dataset
uspto-grants-2004_01
Patent number
US06677462B2

Reaction notes

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