4-Ethylbenzaldehyde → HCID 69220512, compound

HRID 2116497Notes

Reaction equation

HRID 2116497 reaction equation
Br[C:2]1[C:7]([O:8][CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])(C)(C)C.[CH2:25]([C:27]1[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=1)[CH3:26].[Cl-].[NH4+]>C1COCC1.CCCCC>[CH2:25]([C:27]1[CH:34]=[CH:33][C:30]([CH:31]([C:2]2[C:7]([O:8][CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:6][CH:5]=[CH:4][N:3]=2)[OH:32])=[CH:29][CH:28]=1)[CH3:26]

Participants

7

Reactant 4

HCID 208614-EthylbenzaldehydeHCID 25517Ammonium ChlorideHCID 23103610HCID 23103610, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 69220512HCID 69220512, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Next, to a solution of 2-bromo-3-[2-(triethylsilyl)ethoxymethoxy]pyridine (2.0 g, 6.57 mmol) in THF (22 mL), a 1.47 M n-pentane solution of tert-butyllithium (9.6 mL, 14.1 mmol) was slowly added dropwise at −78° C. After 20 minutes, a solution of 4-ethylbenzaldehyde (1.0 g, 7.45 mmol) in THF (5 mL) was added dropwise to the reaction mixture. After stirring at −78° C. for 10 minutes, the reaction mixture was warmed to room temperature and saturated aqueous ammonium chloride was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 4-ethylphenyl-[3-[2-(triethylsilyl)ethoxymethoxy]]pyridin-2-yl-methanol (0.89 g, 38%).

Workup

  1. temperaturethe reaction mixture was warmed to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-7449f885ebfe4d5eb0fe454eeef33e02
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

Loading…