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

HRID 45456Notes

Reaction equation

HRID 45456 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](=[O:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[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]([C:2]2[CH:3]=[C:4]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=2)([OH:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 119949201-(2-(Benzyloxy)biphenyl-3-yl)ethanoneHCID 186686213'-Bromo-2-methoxybiphenylHCID 178418339Butyllithium

Product 1

HCID 582385901-(2-(Benzyloxy)biphenyl-3-yl)-1-(2'-methoxybiphenyl-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 21 (0.7 g, 2.66 mmol) in anhydrous tetrahydrofuran (15 mL) was stirred under nitrogen at −78° C. and 2.5M n-butyllithium in hexanes (1.1 mL, 2.75 mmol) was added at such a rate that the temperature did not exceed −70° C. Stirring was continued at −78° C. for 1 hr when a solution of 20 (0.8 g, 2.66 mmol) in tetrahydrofuran (5 mL) was added at such a rate that the temperature did not exceed −65° C. Stirring was continued at −78° C. for 30 min., then for 2 hrs at room temperature. The reaction mixture was poured onto saturated ammonium chloride (120 mL) and extracted with ethyl acetate (150 mL). The organic extract was washed with water (2×80 mL), dried over sodium sulfate and stripped. The crude 22 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 30 min.
  5. waitfor 2 hrs at room temperature
  6. extractionextracted with ethyl acetate (150 mL)
  7. extractionThe organic extract
  8. washwas washed with water (2×80 mL)
  9. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-1680415de3804a92be1118a011f1932c
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

Loading…