Ammonium Chloride → HCID 67460558, compound

HRID 2116486Notes

Reaction equation

HRID 2116486 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C([Li])CCC.CCCCCC.[CH:22]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][C:25]=1[O:30][CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=[O:23].[Cl-].[NH4+]>O1CCCC1>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([CH:22]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][C:25]=3[O:30][CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[OH:23])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 122213551-Bromo-4-cyclopropylbenzeneHCID 23103619HCID 23103619, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 67460558HCID 67460558, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

To a solution of 4-cyclopropylbromobenzene (synthesized as described in WO0268439; 2.5 g, 0.0127 mol) in tetrahydrofuran (20 ml), a 1.58 mol/L n-butyllithium/n-hexane solution (8.4 ml, 0.0133 mol) was added dropwise at −70° C. over 8 minutes. After stirring at −70° C. for 1 hour, a tetrahydrofuran solution of 4-formyl-3-[2-(trimethylsilyl)ethoxymethoxy]pyridine (4.2 g, 0.0165 mol) was added over 5 minutes and stirred at −70° C. for 2.5 hours. After addition of saturated aqueous ammonium chloride, the reaction mixture was warmed to room temperature and extracted twice with ethyl acetate. The organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50) to give (4-cyclopropylphenyl)-[3-[2-(trimethylsilyl)ethoxymethoxy]pyridin-4-yl]-methanol (2.5 g, 53%) as a brown solid.

Workup

  1. stirringstirred at −70° C. for 2.5 hours
  2. temperaturethe reaction mixture was warmed to room temperature
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50)

Sources & evidence

ORD record
ord-4ea1d1905da14ccf9c01ca6cdc486635
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

Loading…