Ammonium Chloride → (2-(Benzyloxy)biphenyl-3-yl)(2-methoxybiphenyl-3-yl)methanol

HRID 1042510Notes

Reaction equation

HRID 1042510 reaction equation
Br[C:2]1[C:3]([O:14][CH3:15])=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[CH2:21]([O:28][C:29]1[C:34]([CH:35]=[O:36])=[CH:33][CH:32]=[CH:31][C:30]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=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]([CH:35]([C:2]2[C:3]([O:14][CH3:15])=[C:4]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:5]=[CH:6][CH:7]=2)[OH:36])=[CH:33][CH:32]=[CH:31][C:30]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 183474973-Bromo-2-methoxy-1,1'-biphenylHCID 218409602-(Benzyloxy)-[1,1'-biphenyl]-3-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 58238521(2-(Benzyloxy)biphenyl-3-yl)(2-methoxybiphenyl-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2 (0.91 g, 3.46 mmol) in anhydrous tetrahydrofuran (15 mL) was stirred under nitrogen at −78° C. and 2.5M n-butyllithium in hexanes (1.38 mL, 3.46 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 2-(benzyloxy)biphenyl-3-carbaldehyde (1.0 g, 3.46 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 20 min, then for 2 hr at room temperature. The reaction mixture was poured on saturated ammonium chloride (150 mL) and extracted with ethyl acetate (150 mL). The organic extract was washed with water (2×100 mL), dried over sodium sulfate and stripped. The crude 3 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
  5. waitfor 2 hr at room temperature
  6. extractionextracted with ethyl acetate (150 mL)
  7. extractionThe organic extract
  8. washwas washed with water (2×100 mL)
  9. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-e79a83c0f63e48ab83e7f0452f0c612d
Source dataset
uspto-grants-2013_10
Patent number
US08557936B2

Reaction notes

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