Acetic acid 4-[2-(2-cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-isopropyl-phenyl ester → 6-Cyclopentyl-6-[2-(4-hydroxy-3-isopropyl-phenyl)-ethyl]-dihydro-pyran-2,4-dione

HRID 1453063Notes

Reaction equation

HRID 1453063 reaction equation
[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22]C(=O)C)=[C:18]([CH:26]([CH3:28])[CH3:27])[CH:17]=3)[CH2:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[O:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C2(CCC3C=CC(OC(=O)C)=C(CC)C=3)CC(=O)CC(=O)O2)CCCC1>>[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH:26]([CH3:28])[CH3:27])[CH:17]=3)[O:7][C:8](=[O:13])[CH2:9][C:10](=[O:12])[CH2:11]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 58762327Acetic acid 4-[2-(2-cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-isopropyl-phenyl esterHCID 58762607Acetic acid 4-[2-(2-cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-ethyl-phenyl ester

Product 1

HCID 587624326-Cyclopentyl-6-[2-(4-hydroxy-3-isopropyl-phenyl)-ethyl]-dihydro-pyran-2,4-dione

Procedure

The title compound was prepared analogously to Example A(22) where Acetic acid 4-[2-(2-cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-isopropyl-phenyl ester (Example A(94)) was substituted in place of acetic acid 4-[2-(2-cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-ethyl-phenyl ester. 1H NMR (CDCl3): δ 1.24 (d, 6H, J=6.8 Hz), 1.47-1.81 (br m, 8H), 1.87-2.01 (m, 2H), 2.27 (m, 1H), 2.60 (m, 2H), 2.77 (s, 3H), 3.18 (m, 1H), 3.42 (s, 1H), 4.80 (s, 1H), 6.67 (d, 1H, J=8.1 Hz), 6.83 (dd, 1H, J=8.1, 2.3 Hz), 6.94 (d, 1H, J=2.3 Hz). Anal. Calcd. For C21H28O4.0.3H2O: C, 72.09; H, 8.24. Found: C, 72.12; H, 8.23.

Sources & evidence

ORD record
ord-95892ce637be422dace9c7d81be1cc25
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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