1,4-Dioxane → HCID 69428901, compound

HRID 351451Notes

Reaction equation

C(O[O:4][CH2:5][CH:6]1[C:11]([CH3:12])=[C:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=2)[C:9](OS(C(F)(F)F)(=O)=O)=[CH:8][CH2:7]1)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:45][O:46][C:47]1[CH:52]=[CH:51][C:50](B(O)O)=[CH:49][CH:48]=1.[O:56]1CCO[CH2:58][CH2:57]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:57]([O:56][C:5]([CH:6]1[CH:11]([CH3:12])[CH:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=2)[C:9]([C:50]2[CH:51]=[CH:52][C:47]([O:46][CH3:45])=[CH:48][CH:49]=2)=[CH:8][CH2:7]1)=[O:4])[CH3:58]

Participants

Conditions

Temperature: 8 °C

Procedure

Into a mixture of trifluoro-methanesulfonic acid 4-ethylperoxymethyl-5-methyl-6-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-cyclohexa-1,5-dienyl ester (118.5 mg, 0.2219 mmol), Pd (PPh3)4 (6.4 mg, 0.025 eq.) and K3PO4 (70.7 mg, 1.5 eq.) in 1,4-dioxane (5 mL) was bubbled N2 for 10 min. To the reaction mixture was then added 4-methoxy benzene boronic acid (37.1 mg, 0.2441 mmol). The resulting mixture was heated to 8° C. for 16 h, filtered through a plug of silica gel, concentrated and purified on preparative TLC (10% MeOH/DCM) to yield 4-(4-methoxy-phenyl)-6-methyl-5-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-cyclohex-3-enecarboxylic acid ethyl ester as light yellow oil.

Workup

customwas bubbled N2 for 10 min
filtrationfiltered through a plug of silica gel
concentrationconcentrated
custompurified on preparative TLC (10% MeOH/DCM)

Sources & evidence

ORD record: ord-c73194a1528e4fb5ac4b1cb832d3f97b
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183445B2

Reaction notes

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