Ammonium Chloride → HCID 67103683, compound

HRID 45448Notes

Reaction equation

HRID 45448 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]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=O)[CH:25]=1)[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]([CH3:22])([CH3:21])[CH3:23])=[CH:18][CH:17]=[CH:16][C:15]=1[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[CH2:1])[CH:25]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 67103457(2'-(Benzyloxy)-3'-tert-butylbiphenyl-3-yl)(pyridin-2-yl)methanoneHCID 178418339Butyllithium

Product 1

HCID 67103683HCID 67103683, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyltriphenylphosphoniumbromide (1.4 g, 3.9 mmol) in anhydrous tetrahydrofuran (15 mL) was stirred under nitrogen on an ice bath and 2.5 M n-butyllithium in hexanes (1.5 mL, 3.75 mmol) was slowly added. After 20 min. the cold bath was removed and stirring was continued at room temperature for 1 hr. The reaction mixture was cooled on an ice bath and a solution of 11 (0.82 g, 1.95 mmol) in tetrahydrofuran (15 mL) was added at such a rate that the temperature did not exceed 5° C. Stirring was continued overnight at room temperature. The reaction mixture was poured on 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 residue was purified by chromatography on silica (50 g) with 5% ethyl acetate in heptane (3 L) to produce pure 12 (0.13 g, 16%).

Workup

  1. customAfter 20 min. the cold bath was removed
  2. temperatureThe reaction mixture was cooled on an ice bath
  3. customdid not exceed 5° C
  4. stirringStirring
  5. waitwas continued overnight 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
  10. customThe residue was purified by chromatography on silica (50 g) with 5% ethyl acetate in heptane (3 L)

Sources & evidence

ORD record
ord-6796b4a070e94148a0d9de33d169279a
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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