Ammonium Chloride → HCID 67777663, compound

HRID 1026354Notes

Reaction equation

HRID 1026354 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11])=[CH:4][N:3]=1.C([Li])CCC.[Br:24][C:25]1[CH:30]=[C:29]([O:31][CH2:32][O:33][CH3:34])[CH:28]=[CH:27][C:26]=1[CH2:35][C:36](=[O:38])[CH3:37].[Cl-].[NH4+]>CCOCC>[Br:24][C:25]1[CH:30]=[C:29]([O:31][CH2:32][O:33][CH3:34])[CH:28]=[CH:27][C:26]=1[CH2:35][C:36]([C:2]1[CH:7]=[CH:6][C:5]([O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11])=[CH:4][N:3]=1)([OH:38])[CH3:37]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 67777995HCID 67777995, compoundHCID 86666326HCID 86666326, compoundHCID 178418339Butyllithium

Product 1

HCID 67777663HCID 67777663, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2-bromo-5-(triisopropylsilyloxy)pyridine (26.6 g) in ether (80 mL) at −78° C. was added n-butyllithium (2.5 M in hexane, 32.2 mL) dropwise. After being stirred at the same temperature for 10 min, a solution of 1-(2-bromo-4-(methoxymethoxy)phenyl)propan-2-one (11 g) in diethylether (40 mL) was added dropwise. The mixture was stirred at −78° C. for 5 hr, and poured into iced saturated ammonium chloride and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to afford the title compound (9.6 g).

Workup

  1. stirringThe mixture was stirred at −78° C. for 5 hr
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-e0ffe592ed0f4f439328f44dbdd7f1a9
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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