Ammonium Chloride → HCID 57443972, compound

HRID 1172855Notes

Reaction equation

HRID 1172855 reaction equation
CON(C)[C:4]([C:6]1[CH:19]=[CH:18][C:9]2[CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:12][C:8]=2[CH:7]=1)=[O:5].[Li][CH3:22].[Cl-].[NH4+]>C1COCC1>[C:4]([C:6]1[CH:19]=[CH:18][C:9]2[CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:12][C:8]=2[CH:7]=1)(=[O:5])[CH3:22]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 59424233HCID 59424233, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 57443972HCID 57443972, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-{[methoxy(methyl)amino]carbonyl}-1-benzothiophene-2-carboxylate (0.07 g, 0.22 mmol) in THF (3 mL) at −78° C. was added MeLi (0.15 mL, 1.6 M in Et2O, 0.24 mmol). The reaction was stirred for 1 h at −78° C. before saturated ammonium chloride solution was added to quench the reaction. At which time the reaction mixture was allowed to warm to room temperature and then extracted with a mixture of hexane:ethyl acetate solution (3:1) (3×). The combined organic layers was dried over Na2SO4, filtered, and concentrated in vacuo. The crude mixture was chromatographed to provide the ketone. 1H NMR (CDCl3, 600 MHz) δ 8.46 (s, 1H), 8.07 (s, 1H), 7.98 (dd, J=8.2, 1.2 Hz, 1H), 7.92 (m, 1H), 4.42 (q, J=7.1 Hz, 2H), 2.69 (s, 3H), 1.42 (t, J=7.2 Hz, 3H). MS: cal'd (MH+) 249, exp (MH+) 249.

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. extractionextracted with a mixture of hexane
  5. dry with materialThe combined organic layers was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude mixture was chromatographed

Sources & evidence

ORD record
ord-eaadea50c0954a46ac691f53ce319826
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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