1,4-Dioxane → Ethyl acetate hexane

HRID 1426265Notes

Reaction equation

HRID 1426265 reaction equation
[C:1]([C:5]1C=C(C2N=C(C)C3C(C=2)=CC([O:21]C)=C(OC)C=3)[CH:8]=[CH:9][CH:10]=1)(C)(C)[CH3:2].[O:26]1[CH2:31][CH2:30]O[CH2:28][CH2:27]1>>[CH3:28][CH2:27][O:26][C:31]([CH3:30])=[O:21].[CH3:2][CH2:1][CH2:5][CH2:10][CH2:9][CH3:8]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 67995172HCID 67995172, compound

Product 1

HCID 21226206Ethyl acetate hexaneYield 62%

Procedure

3-(3-(tert-Butyl)phenyl)-6,7-dimethoxy-1-methylisoquinoline (153 mg) and SeO2 (61 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 (97 mg, 62% yield). 1H NMR (400 MHz) (CDCl3) δ 10.40 (s, 1H), 8.67 (s, 1H), 8.14 (s, 1H), 8.08 (s, 1H), 7.90 (dt, J=4 Hz, J=4 Hz, 1H), 7.42-7.40 (m, 2H), 7.13 (s, 1H), 4.04 (s, 3H), 4.00 (s, 3H), 1.36 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ 196.96, 153.20, 152.67, 151.82, 150.35, 146.98, 138.51, 135.43, 128.67, 125.91, 124.05, 123.78, 122.07, 120.08, 104.95, 103.49, 56.30, 56.07, 34.95, 31.46.

Workup

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

Sources & evidence

ORD record
ord-158ee44cc23c4f13acaf59ef036410b0
Source dataset
uspto-grants-2015_01
Patent number
US08933096B2

Reaction notes

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