Trifluoroacetic acid → HCID 58762323, compound

HRID 858777Notes

Reaction equation

HRID 858777 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([CH2:24][CH2:25][C:26]2([CH:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[O:31][C:30](=[O:32])[CH2:29][C:28](=[O:33])[CH2:27]2)[CH:12]=[C:13]([CH2:22][CH3:23])[C:14]=1[O:15]COCCOC>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[C:11]([CH2:24][CH2:25][C:26]2([CH:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[O:31][C:30](=[O:32])[CH2:29][C:28](=[O:33])[CH2:27]2)[CH:12]=[C:13]([CH2:22][CH3:23])[C:14]=1[OH:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58762746HCID 58762746, compound

Product 1

HCID 58762323HCID 58762323, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.07 mL, 0.88 mmol) was added to a solution of 6-{2-[3-Chloro-5-ethyl-4-(2-methoxy-ethoxymethoxy)-phenyl]-ethyl}-6-cyclopentyl-dihydro-pyran-2,4-dione (0.2 g, 0.44 mmol) dissolved in CH2Cl2 (4 mL). The reaction mixture was stirred for 2 hours at room temperature and then partitioned between H2O and EtOAc. The organic extracts were washed with brine, dried over Na2SO4 and concentrated to an oil. The oil was purified by flash column chromatography (0% to 30% EtOAc in hexanes) to give the title compound as a solid. (0.12 g, 75%). 1H NMR (400 MHz, CDCl3): δ 1.21 (t, J=7.6 Hz, 3 H), 1.58–173 (br m, 8 H), 1.92 (m, 2 H), 2.26 (m, 1 H), 2.57 (m, 2 H), 2.65 (q, J=7.6 Hz, 2 H), 2.76 (s, 2 H), 3.43 (s, 2 H), 5.47 (s, 1 H), 6.81 (s, 1 H), 6.95 (s, 1 H). MS: C20H24O4Cl (M−H) 363.10.

Workup

  1. custompartitioned between H2O and EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to an oil
  5. customThe oil was purified by flash column chromatography (0% to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f53c0736cb4b4d2b900babfb1a36987b
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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