1,4-Dioxane → Ethyl acetate hexane

HRID 1426260Notes

Reaction equation

HRID 1426260 reaction equation
[C:1]([C:5]1C=C(C2C=CC=C(C3N=C(C)C4C(C=3)=CC([O:27]C)=C(OC)C=4)C=2)[CH:8]=[CH:9][CH:10]=1)(C)(C)[CH3:2].[O:32]1[CH2:37][CH2:36]O[CH2:34][CH2:33]1>>[CH3:34][CH2:33][O:32][C:37]([CH3:36])=[O:27].[CH3:2][CH2:1][CH2:5][CH2:10][CH2:9][CH3:8]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 67996216HCID 67996216, compound

Product 1

HCID 21226206Ethyl acetate hexaneYield 58%

Procedure

3-(3′-(tert-Butyl)-[1,1′-biphenyl]-3-yl)-6,7-dimethoxy-1-methylisoquinoline (92 mg) and SeO2 (25 mg, 1.2 eq.) in 5 mL anhydrous dioxane were refluxed at 102° C. for 3 hours. Solution was then cooled to room temperature and filtered to remove precipitate. Resulting filtrate was concentrated. Chromatography achieved using ISCO max gradient 30% EtOAc/hexane yielding product as a yellow solid (55 mg, 58% yield). 1H NMR (400 MHz) (CDCl3) δ 10.39 (s, 1H), 8.66 (s, 1H), 8.31 (s, 1H), 8.12 (s, 1H), 8.07 (d, J=4 Hz, 1H), 7.63 (s, 1H), 7.59 (d, J=8 Hz, 1H), 7.53 (t, J=12 Hz, 1H), 7.46-7.44 (m, 1H), 7.36-7.35 (m, 2H), 7.11 (s, 1H), 4.03 (s, 3H), 3.99 (s, 3H), 1.34 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ 196.86, 153.26, 152.79, 151.71, 149.69, 147.04, 142.67, 141.02, 139.21, 135.42, 129.29, 128.54, 127.80, 125.81, 125.52, 124.61, 124.54, 124.47, 122.19, 120.07, 104.99, 103.52, 56.31, 56.07, 34.89, 31.47.

Workup

  1. filtrationfiltered
  2. customto remove precipitate
  3. concentrationResulting filtrate was concentrated

Sources & evidence

ORD record
ord-0298e174fae84173bb91ff7d98b3597c
Source dataset
uspto-grants-2015_01
Patent number
US08933096B2

Reaction notes

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