Triethylamine → HCID 67781535, compound

HRID 1779048Notes

Reaction equation

HRID 1779048 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1C(=O)C=[N+]=[N-].CCN(CC)CC.C[CH2:22][O:23][C:24]([CH3:26])=[O:25]>C1COCC1.CO.C([O-])(=O)C1C=CC=CC=1.[Ag+]>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH2:26][C:24]([O:23][CH3:22])=[O:25]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86712690HCID 86712690, compound

Product 1

HCID 67781535HCID 67781535, compound

Reagents, catalysts & solvents 3

HCID 164649Silver benzoateCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-bromo-4-methylphenyl)-2-diazoethanone (A83) (667 mg, 2.79 mmol) in THF (4.3 mL) and MeOH (4.3 mL) was added a solution of silver benzoate (96 mg, 0.42 mmol) in Et3N (1.13 mL, 11.2 mmol). The resulting mixture was stirred for 2 hours at room temperature then passed through a plug of silica gel eluting with 50% EtOAc in petroleum benzine 40-60° C. The eluent was evaporated in vacuo and the residue was adsorbed onto silica gel and separated using silica gel column chromatography (Biotage Isolera, 25 g SiO2 cartridge, 0-50% EtOAc in petroleum benzine 40-60° C.) to give the title compound A84 as a clear oil (678 mg, >99%); 1H NMR (400 MHz, CDCl3) δ 7.39 (d, J=0.7 Hz, 1H), 7.16 (d, J=7.8 Hz, 1H), 7.07 (dd, J=7.7, 1.0 Hz, 1H), 3.76 (s, 2H), 3.70 (s, 3H), 2.30 (s, 3H). LCMS-A: rt 6.070 min.

Workup

  1. customThe eluent was evaporated in vacuo
  2. customseparated
  3. customsilica gel column chromatography (Biotage Isolera, 25 g SiO2 cartridge, 0-50% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-d54ee377ad5745cebbde1dff11f83396
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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