Ammonium Chloride → 1-(2-(Benzyloxy)-3-tert-butylphenyl)-1-(2'-methoxybiphenyl-3-yl)ethanol

HRID 45463Notes

Reaction equation

HRID 45463 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[CH2:21]([O:28][C:29]1[C:34]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=1[C:39](=[O:41])[CH3:40])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:21]([O:28][C:29]1[C:34]([C:35]([CH3:36])([CH3:37])[CH3:38])=[CH:33][CH:32]=[CH:31][C:30]=1[C:39]([C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1)([OH:41])[CH3:40])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 160883251-(2-(Benzyloxy)-3-tert-butylphenyl)ethanoneHCID 186686213'-Bromo-2-methoxybiphenylHCID 178418339Butyllithium

Product 1

HCID 582385601-(2-(Benzyloxy)-3-tert-butylphenyl)-1-(2'-methoxybiphenyl-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3′-bromo-2-methoxybiphenyl (1.31 g, 5 mmol) in anhydrous tetrahydrofuran (20 mL) was stirred at −78° C. and 2.5M n-butyllithium in hexanes (2 mL, 5 mmol) was added at such a rate that the temperature did not exceed −70° C. Stirring was continued at −78° C. for 1 hr. A solution of 1-(2-(benzyloxy)-3-tert-butylphenyl)ethanone (1.41 g, 5 mmol) in tetrahydrofuran (8 mL) was added at such a rate that the temperature did not exceed −65° C. Stirring was continued at −78° C. for 20 min and at room temperature for 2 hr. The reaction mixture was poured onto saturated ammonium chloride (80 mL) and extracted with ethyl acetate (150 mL). The organic extract was washed with water (2×80 mL). The organic layer was dried over sodium sulfate, filtered and the solvent was removed on a rotary evaporator. The crude product 27 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 at −78° C. for 20 min and at room temperature for 2 hr
  5. extractionextracted with ethyl acetate (150 mL)
  6. extractionThe organic extract
  7. washwas washed with water (2×80 mL)
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-e288fb5b9d4f4426b6da51fc6544955f
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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