Ammonium Chloride → (2-(Benzyloxy)-3-tert-butylphenyl)(3-(pyridin-2-yl)phenyl)methanol

HRID 45438Notes

Reaction equation

HRID 45438 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[CH2:19]([O:26][C:27]1[C:34]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:28]=1[CH:29]=[O:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:19]([O:26][C:27]1[C:34]([C:35]([CH3:36])([CH3:38])[CH3:37])=[CH:33][CH:32]=[CH:31][C:28]=1[CH:29]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:3]=1)[OH:30])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 111155062-(3-Bromophenyl)pyridineHCID 115435672-(Benzyloxy)-3-(tert-butyl)benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 58238562(2-(Benzyloxy)-3-tert-butylphenyl)(3-(pyridin-2-yl)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(3-bromophenyl)pyridine (2.4 g, 10.25 mmol) in anhydrous tetrahydrofuran (25 mL) was stirred at −78° C. and 2.5M n-butyllithium in hexanes (4.1 mL, 10.25 mmol) was added at such a rate that temperature did not exceed −70° C. Stirring was continued on the cold bath for 30 min and a solution of 2-(benzyloxy)-3-tert-butylbenzaldehyde (2.75 g, 10.25 mmol) in tetrahydrofuran (12 mL) was added at such a rate that temperature did not exceed −65° C. Stirring was continued on the cold bath for 20 min and 2 hr at room temperature. The reaction mixture was poured on saturated ammonium chloride (250 mL) and extracted with ethyl acetate (350 mL). The organic extract was washed with water (2×100 mL) and dried over sodium sulfate. The solvent was removed on a rotary evaporator and the crude product was used as such in the next step.

Workup

  1. customdid not exceed −70° C
  2. customdid not exceed −65° C
  3. stirringStirring
  4. waitwas continued on the cold bath for 20 min and 2 hr at room temperature
  5. extractionextracted with ethyl acetate (350 mL)
  6. extractionThe organic extract
  7. washwas washed with water (2×100 mL)
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-5141c601919943c3abc47b2b3f3ac056
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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