Pyridine → 2-[Bis(methylthio)methylene]-4-(5,5-dimethylhexyl)-4-methylnaphthalene-1,3(2h,4h)-dione

HRID 494539Notes

Reaction equation

[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1([CH3:19])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[CH:9][C:8]1=[O:18].N1C=CC=CC=1.COS([O-])(=O)=O.[CH3:34][S:35][C:36](=[S+]C)[S:37][CH3:38]>O1CCOCC1>[CH3:34][S:35][C:36]([S:37][CH3:38])=[C:9]1[C:8](=[O:18])[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][C:2]([CH3:21])([CH3:20])[CH3:1])([CH3:19])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:17]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of Example 35G (1.06 g, 3.70 mmol) and pyridine (2.40 mL, 29.6 mmol) in 1,4-dioxane (15 mL) was treated with [bis(methylsulfanyl)methylene](methyl)sulfonium methyl sulfate (3.93 g, 14.8 mmol) and stirred at 100° C. for 1 hour. The mixture was cooled to 25° C. and partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water and brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane followed by 5%, 10%, and 20% ethyl acetate in hexane to give the title compound (1.45 g, 99%). 1H NMR (300 MHz, CDCl3): δ ppm 0.78 (m, 10 H) 1.01 (m, 5 H) 1.56 (m, 3 H) 1.77 (m, 1 H) 2.23 (m, 1 H) 2.56 (m, 6 H) 7.39 (m, 2 H) 7.56 (m, 1 H) 8.21 (m, 1 H). MS (ESI+) m/z 391 (M+H)+.

Workup

temperatureThe mixture was cooled to 25° C.
custompartitioned between ethyl acetate and water
washThe ethyl acetate layer was washed with water and brine
dry with materialdried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel eluting with hexane

Sources & evidence

ORD record: ord-62f3b35d5e8547a291fa3a506981ed0b
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538105B2

Reaction notes

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