HCID 10431947, compound → HCID 10474324, compound

HRID 1453021Notes

Reaction equation

HRID 1453021 reaction equation
[C:1]([C:5]1([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]3([CH:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[O:23][C:22](=[O:24])[CH2:21][C:20](=[O:25])[CH2:19]3)=[CH:12][CH:11]=2)OCC[O:6]1)([CH3:4])([CH3:3])[CH3:2]>CC(C)=O>[CH:26]1([C:18]2([CH2:17][CH2:16][C:13]3[CH:14]=[CH:15][C:10]([C:5](=[O:6])[C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:11][CH:12]=3)[O:23][C:22](=[O:24])[CH2:21][C:20](=[O:25])[CH2:19]2)[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

3

Reactant 1

HCID 10431947HCID 10431947, compound

Product 1

HCID 10474324HCID 10474324, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 6-{2-[4-(2-tert-Butyl-[1,3]dioxolan-2-yl)-phenyl]-ethyl}-6-cyclopentyl-dihydro-pyran-2,4-dione from Example A(34), (0.173 g) in acetone (1 mL) was added Amberlyst 15 (0.05 g). The reaction mixture was stirred at room temperature overnight, and then filtrated. The solvent was removed under reduced pressure. The residue was purified by flash chromatography (40% EtOAc in Hexanes) to yield the product as a white foam (0.04 g, 95%). 1H NMR (CDCl3): δ 1.35 (s, 9H), 1.47-1.84 (m, 8H), 1.91-2.03 (m, 2H), 2.25-2.34 (m, 1H), 2.72 (t, J=8.0 Hz, 2H), 2.78 (s, 2H), 3.44 (s, 2H), 7.18 (d, J=8.2 Hz, 2H), 7.67 (d, J=8.2 Hz, 2H). Anal. Calcd. For C23H30O4: C, 74.56; H, 8.16. Found: C, 74.86; H, 8.43. ESIMS (MH+): 371

Workup

  1. filtrationfiltrated
  2. customThe solvent was removed under reduced pressure
  3. customThe residue was purified by flash chromatography (40% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-e64b6a2a92e94979ab6d8ac37386fda8
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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