Ammonium Chloride → 4-{4-[1-Ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenylethynyl}-tetrahydro-pyran-4-ol

HRID 547036Notes

Reaction equation

HRID 547036 reaction equation
C([Li])CCC.[CH2:6]([C:8]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([CH3:27])[CH:21]=1)([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[CH:18])=[C:13]([CH3:19])[CH:12]=1)[CH2:9][CH3:10])[CH3:7].[O:28]1[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][CH2:29]1.[Cl-].[NH4+]>O1CCCC1>[CH2:6]([C:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][C:31]2([OH:34])[CH2:32][CH2:33][O:28][CH2:29][CH2:30]2)=[C:13]([CH3:19])[CH:12]=1)([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([CH3:27])[CH:21]=1)[CH2:9][CH3:10])[CH3:7]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 585982954-[1-Ethyl-1-(4-ethynyl-3-methyl-phenyl)-propyl]-2-methyl-phenolHCID 178418339Butyllithium

Product 1

HCID 577089754-{4-[1-Ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenylethynyl}-tetrahydro-pyran-4-olYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (2.71 M solution in hexane, 3.15 mL, 8.55 mmol) was added to a solution of 4-[1-ethyl-1-(4-ethynyl-3-methyl-phenyl)-propyl]-2-methyl-phenol (Example 1-(3); 1.0 g, 3.42 mmol) in tetrahydrofuran (30 mL) in a nitrogen atmosphere at 0° C., and the mixture was stirred for 15 minutes. Then, tetrahydropyran-4-one (685 mg, 6.84 mmol) was added to the reaction mixture, which was further stirred at 0° C. for 30 minutes. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 30:70) to give the target compound as a colorless oil (0.97 g, 72%).

Workup

  1. stirringwas further stirred at 0° C. for 30 minutes
  2. extractionfollowed by extraction with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 30:70)

Sources & evidence

ORD record
ord-cc2036e4c2c54c169ffcb05ce28906e9
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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