2,6-Lutidine → HCID 86720753, compound

HRID 2167705Notes

Reaction equation

HRID 2167705 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[Br:39]N1C(=O)CCC1=O>O.C(Cl)(Cl)Cl>[Br:39][CH2:17][C:16]([C:13]1[CH:12]=[CH:11][C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:15][CH:14]=1)=[O:18]

Participants

7

Reactant 4

HCID 79372,6-LutidineHCID 65367Trimethylsilyl triflateHCID 67184N-bromobutanimideHCID 13294359HCID 13294359, compound

Product 1

HCID 86720753HCID 86720753, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a chloroform (7.5 mL) solution of 1-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]ethanone (0.23 g), under ice cooling in a nitrogen atmosphere, 2,6-lutidine (0.17 mL) and trimethylsilyl trifluoromethanesulfonate (0.19 mL) were added, and the resultant was stirred for 30 minutes. Then, N-bromosuccinimide (0.17 g) was added thereto, and the resultant was stirred for 30 minutes under ice cooling. Water was added to the reaction solution, and the resultant was stirred for 10 minutes, followed by extraction with chloroform. An organic layer was separated using a phase separator, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=100/0→75/25) to obtain the title compound (0.26 g) as a colorless oil.

Workup

  1. stirringthe resultant was stirred for 30 minutes under ice cooling
  2. stirringthe resultant was stirred for 10 minutes
  3. extractionfollowed by extraction with chloroform
  4. customAn organic layer was separated
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (OH-type silica gel; hexane/ethyl acetate-gradient elution=100/0→75/25)

Sources & evidence

ORD record
ord-04b3c68e887945fc831bcdae322c5145
Source dataset
uspto-grants-2015_06
Patent number
US09045466B2

Reaction notes

Loading…