1,1-dibutyl-4-hydroxy-2(1H)-naphthalenone → 2-[bis(methylsulfanyl)methylene]-4,4-dibutyl-1,3(2H,4H)-naphthalenedione

HRID 494455Notes

Reaction equation

[CH2:1]([C:5]1([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[CH:7][C:6]1=[O:16])[CH2:2][CH2:3][CH3:4].COS([O-])(=O)=O.[CH3:27][S:28][C:29](=[S+]C)[S:30][CH3:31]>O1CCOCC1>[CH3:27][S:28][C:29]([S:30][CH3:31])=[C:7]1[C:6](=[O:16])[C:5]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:1][CH2:2][CH2:3][CH3:4])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:15]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of the product of Example 5B (25 mg, 0.092 mmol) in dioxane (4 mL) was treated with the product of Example 5A (71 mg, 0.27 mmol) and stirred at 100° C. for 2 hours, cooled to 25° C., diluted with ice water and extracted with ethyl acetate (3×). The combined organic layers were washed with water (3×) and saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound. 1H NMR (300 MHz, DMSO-d6): δ 8.05 (m, 1 H), 7.66 (m, 1 H), 7.56 (d, J=7.72 Hz, 1 H), 7.43 (t, J=6.80 Hz, 1 H), 2.51 (m, 6 H), 2.10 (m, 2 H), 1.82 (m, 2 H), 1.09 (m, 4 H), 0.69 (m, 10 H).

Workup

temperaturecooled to 25° C.
extractionextracted with ethyl acetate (3×)
washThe combined organic layers were washed with water (3×) and saturated sodium chloride solution
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-31b6de896dda4e9894820c69ddd5a19d
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538105B2

Reaction notes

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