Potassium Carbonate → 6-Cyclopentyl-6-[2-(5-ethyl-4-hydroxy-2-propoxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione

HRID 1438192Notes

Reaction equation

[CH:1]1([C:6]([OH:32])([CH2:17][CH2:18][C:19]2[CH:24]=[C:23]([CH2:25][CH3:26])[C:22]([OH:27])=[CH:21][C:20]=2[O:28][CH2:29][CH2:30][CH3:31])[CH2:7][C:8]2[O:13]C(C)(C)O[C:10](=[O:16])[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH:1]1([C:6]2([CH2:17][CH2:18][C:19]3[CH:24]=[C:23]([CH2:25][CH3:26])[C:22]([OH:27])=[CH:21][C:20]=3[O:28][CH2:29][CH2:30][CH3:31])[O:32][C:10](=[O:16])[CH2:9][C:8](=[O:13])[CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 45 °C

Procedure

6-[2-Cyclopentyl-4-(5-ethyl-4-hydroxy-2-propoxy-phenyl)-2-hydroxy-butyl]-2,2-dimethyl-[1,3]dioxin-4-one (0.8 g, 1.8 mmol,) was dissolved in methanol (15 mL), treated with potassium carbonate (0.74 g, 5.4 mmol) and heated at 45° C. under N2 for 90 mins. The reaction mixture was partitioned between H2O and IPE. The aqueous layer was made acidic with 1N HCl and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to give the product as a yellow foam (0.5 g, 72% yield). 1H NMR (400 MHz, CDCl3): δ 1.02 (t, J=7.3 Hz, 3H), 1.19 (t, J=7.6 Hz, 3H), 1.41-1.87 (br m, 11H), 1.95 (m, 1H), 2.32 (m, 1H), 2.49-2.80 (m, 6H), 3.41 (m, 2H), 3.85 (m, 2H), 4.62 (s, 1H), 6.33 (s, 1H), 6.80 (s, 1H).

Workup

customThe reaction mixture was partitioned between H2O and IPE
extractionextracted with EtOAc
washThe organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-383342abfd6a4a3e9b4193a49cc96642
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622605B2

Reaction notes

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