Triethylamine → Ethyl acetate hexane

HRID 1426256Notes

Reaction equation

HRID 1426256 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1OC)C(C)=NC(O)=C2.CCN([CH2:22][CH3:23])CC.[O:24](S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O>C(Cl)Cl>[CH3:12][CH2:3][O:2][C:22]([CH3:23])=[O:24].[CH3:5][CH2:4][CH2:3][CH2:12][CH2:11][CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 178486704HCID 178486704, compound

Product 1

HCID 21226206Ethyl acetate hexaneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

6,7-Dimethoxy-1-methylisoquinolin-3-ol (540 mg) and Et3N (0.9 mL, 2 eq.) in DCM were cooled to −78° C. Tf2O (0.64 mL, 1.2 eq.) was slowly added to the mixture and was stirred for 30 minutes at −78° C. Reaction was then quickly diluted with additional DCM and washed with saturated NaHCO3. Organic layer was dried over sodium sulfate and concentrated. Chromatography achieved using ISCO max gradient 30% EtOAc/hexane yielding product as a white solid (737 mg, 85% yield). 1H NMR (400 MHz) (CDCl3) δ 7.29 (s, 1H), 7.29 (s, 1H), 7.12 (s, 1H), 4.07 (s, 3H), 4.07 (s, 3H), 2.90 (s, 3H). 13C NMR (100 MHz) (CDCl3) δ 156.54, 153.80, 150.67, 135.47, 123.35, 107.62, 105.39, 103.73, 56.23, 56.11, 22.03.

Workup

  1. customReaction
  2. washwashed with saturated NaHCO3
  3. dry with materialOrganic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dc544bbfc6c946a4bb079235ebc1f975
Source dataset
uspto-grants-2015_01
Patent number
US08933096B2

Reaction notes

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