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

HRID 45442Notes

Reaction equation

HRID 45442 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH:22]=1)=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33]1([Li])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH:22]=1)[OH:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 58238568(2-(Benzyloxy)-3-tert-butylphenyl)(3-(pyridin-2-yl)phenyl)methanoneHCID 178506676HCID 178506676, compound

Product 1

HCID 58238572(2-(Benzyloxy)-3-tert-butylphenyl)(phenyl)(3-(pyridin-2-yl)phenyl)methanolYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2-(benzyloxy)-3-tert-butylphenyl)(3-(pyridin-2-yl)phenyl)methanone (0.96 g, 2.28 mmol) in anhydrous tetrahydrofuran (20 mL) was stirred at −78° C. under nitrogen and 1.8 M phenyllithium (2 mL, 3.6 mmol) was added at such a rate that the temperature did not exceed −70° C. Stirring was continued at −78° C. for 30 min for 1 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 product was purified by chromatography on silica (60 g) with 5% ethyl acetate in heptane (1 L), then 7.5% (2 L) to afford 6 (1.14 g, 100%). This material contains a minor impurity and it was used as such in the next step.

Workup

  1. customdid not exceed −70° C
  2. extractionextracted with ethyl acetate (150 mL)
  3. extractionThe organic extract
  4. washwas washed with water (2×100 mL)
  5. dry with materialdried over sodium sulfate
  6. customThe crude product was purified by chromatography on silica (60 g) with 5% ethyl acetate in heptane (1 L)

Sources & evidence

ORD record
ord-786ab3158c404c2b8c4bb4c38161bc2c
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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