Ammonium Chloride → HCID 58238565, compound

HRID 45440Notes

Reaction equation

HRID 45440 reaction equation
[CH2:1]([Li])CCC.[CH2:6]([O:13][C:14]1[C:19]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=1[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[CH:27]=1)=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:6]([O:13][C:14]1[C:19]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=1[C:24]([C:26]1[CH:27]=[C:28]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[CH:29]=[CH:30][CH:31]=1)=[CH2:1])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 58238568(2-(Benzyloxy)-3-tert-butylphenyl)(3-(pyridin-2-yl)phenyl)methanoneHCID 178418339Butyllithium

Product 1

HCID 58238565HCID 58238565, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl triphenylphosphonium bromide (2.2 g, 6.17 mmol) was suspended in anhydrous tetrahydrofuran (20 mL) and stirred under nitrogen on an ice bath. 2.5M n-Butyllithium in hexanes (2.3 mL, 5.75 mmol) was added at such a rate that temperature did not exceed 3° C. Stirring was continued at room temperature for 1 hr. The reaction mixture was cooled on an ice bath and a solution of 4 (1.3 g, 3.08 mmol) in tetrahydrofuran (8 mL) was added at such a rate that temperature did not exceed 3° C. Stirring was continued at room temperature overnight. 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 (2×80 mL) and dried over sodium sulfate. The solvent was removed on a rotary evaporator and the crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in heptane (2 L), then 4% (4 L) to produce 5 (1.18 g, 91%).

Workup

  1. customdid not exceed 3° C
  2. stirringStirring
  3. temperatureThe reaction mixture was cooled on an ice bath
  4. customdid not exceed 3° C
  5. stirringStirring
  6. waitwas continued at room temperature overnight
  7. extractionextracted with ethyl acetate (150 mL)
  8. extractionThe organic extract
  9. washwas washed with water (2×80 mL)
  10. dry with materialdried over sodium sulfate
  11. customThe solvent was removed on a rotary evaporator
  12. customthe crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in heptane (2 L)

Sources & evidence

ORD record
ord-431bf375e98c4ab59b6c8b737642ae15
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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