Potassium Carbonate → 2-(4-((4-Ethoxy-2,3-difluorophenoxy)methyl)cyclohexyl)-6-propyldecahydronaphthalene

HRID 1257946Notes

Reaction equation

C1(C)C=CC(S(OC[CH:12]2[CH2:17][CH2:16][CH:15]([CH:18]3[CH2:27][CH2:26][CH:25]4[CH:20]([CH2:21][CH2:22][CH:23]([CH2:28][CH2:29][CH3:30])[CH2:24]4)[CH2:19]3)[CH2:14][CH2:13]2)(=O)=O)=CC=1.[CH2:32]([O:34][C:35]1[CH:40]=[CH:39][C:38](O)=[C:37]([F:42])[C:36]=1[F:43])[CH3:33].[C:44](=[O:47])([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:32]([O:34][C:35]1[CH:40]=[CH:39][C:38]([O:47][CH2:44][CH:12]2[CH2:13][CH2:14][CH:15]([CH:18]3[CH2:27][CH2:26][CH:25]4[CH:20]([CH2:21][CH2:22][CH:23]([CH2:28][CH2:29][CH3:30])[CH2:24]4)[CH2:19]3)[CH2:16][CH2:17]2)=[C:37]([F:42])[C:36]=1[F:43])[CH3:33]

Participants

Conditions

Temperature: 70 °C

Procedure

(4-(6-Propyldecahydronaphthalene-2-yl)cyclohexyl)methyl p-toluenesulfonate (3.5 g) prepared in the tenth step was dissolved in DMF (50 ml). 4-Ethoxy-2,3-difluorophenol (1.6 g) and potassium carbonate (2.2 g) were added, and the mixture was stirred at 70° C. for 5 hours. The reaction mixture was washed with water, and dried over anhydrous magnesium sulfate. The DMF was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-heptane=1/20 by volume) and then by recrystallization (solvent: Solmix/n-heptane=1/4 by volume) to give 2-(4-((4-ethoxy-2,3-difluorophenoxy)methyl)cyclohexyl)-6-propyldecahydronaphthalene (2.1 g).

Workup

washThe reaction mixture was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationThe DMF was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-heptane=1/20 by volume)
customby recrystallization (solvent: Solmix/n-heptane=1/4 by volume)

Sources & evidence

ORD record: ord-7497f8b097ad431cbfd3e80f7e1522fe
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08465674B2

Reaction notes

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