1,4-Dioxane → Ethyl acetate hexane

HRID 1426259Notes

Reaction equation

HRID 1426259 reaction equation
[C:1]([C:5]1C=C[C:8](C2C=CC=C(C3N=C(C)C4C(C=3)=CC([O:27]C)=C(OC)C=4)C=2)=[CH:7][CH:6]=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][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 70652024HCID 70652024, compound

Product 1

HCID 21226206Ethyl acetate hexaneYield 77%

Procedure

3-(4′-(tert-Butyl)-[1,1′-biphenyl]-3-yl)-6,7-dimethoxy-1-methylisoquinoline (100 mg) and SeO2 (32 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 (80 mg, 77% yield). 1H NMR (400 MHz) (CDCl3) δ 10.40 (s, 1H), 8.68 (s, 1H), 8.34 (m, 1H), 8.14 (s, 1H), 8.07 (d, J=8 Hz, 1H), 7.59 (d, J=8 Hz, 3H), 7.52 (t, J=16 Hz, 1H), 7.45 (d, J=8 Hz, 2H), 7.13 (s, 1H), 4.05 (s, 3H), 4.00 (s, 3H), 1.32 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ 196.81, 153.33, 152.83, 149.76, 141.84, 139.20, 138.29, 135.44, 129.26, 127.43, 126.95, 125.76, 125.59, 125.35, 122.19, 120.01, 104.99, 103.59, 56.29, 56.02, 34.57, 31.38.

Workup

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

Sources & evidence

ORD record
ord-b66060cf9e204f6ebda4f5cdef2291d1
Source dataset
uspto-grants-2015_01
Patent number
US08933096B2

Reaction notes

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