Trimethylsilyl triflate → HCID 57458152, compound

HRID 1693061Notes

Reaction equation

HRID 1693061 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([O:8][CH3:9])[CH:7]=1.ClC(Cl)(Cl)C(=N)O[CH2:15][N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:26].FC(F)(F)S(O[Si](C)(C)C)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH3:10])=[CH:4][C:3]=1[CH2:15][N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:26]

Participants

5

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 2928585-CHLORO-2-METHYLANISOLEHCID 11347819HCID 11347819, compound

Product 1

HCID 57458152HCID 57458152, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-2-methylanisole (200 mg, 1.28 mmol, purchased from APOLLO) and (1,3-dioxoisoindolin-2-yl)methyl 2,2,2-trichloroacetimidate (411 mg, 1.28 mmol, Synthesis, 2003, 7, 1065-1070) in DCM (30 mL) was added trimethylsilyl trifluoromethansulfonate (14.2 mg, 0.064 mmol) at room temperature under nitrogen. After stirring for 3 hours at room temperature, the reaction mixture was quenched with solid potassium carbonate and evaporated. The residue was chromatographed on a column of silica gel, eluting with EtOAc-Hexane=1:5 to 1:3, to give the title compound (174 mg, 43%) as white solid. 1H NMR (300 MHz, CDCl3) δ ppm 2.11 (3H, s), 3.79 (3H, s), 4.91 (2H, s), 6.81 (1H, s), 7.05 (1H, s), 7.60-7.80 (2H, m), 7.80-8.00 (2H, m). MS (ESI) m/z not observed M+ peak.

Workup

  1. customthe reaction mixture was quenched with solid potassium carbonate
  2. customevaporated
  3. customThe residue was chromatographed on a column of silica gel
  4. washeluting with EtOAc-Hexane=1:5 to 1:3

Sources & evidence

ORD record
ord-b6eb8dcf1d4e4592a955dc84ea54cf35
Source dataset
uspto-grants-2012_04
Patent number
US08158650B2

Reaction notes

Loading…