Sodium bis(2-methoxyethoxy)aluminiumhydride → 4-((E)-2-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl}-vinyl)-tetrahydro-pyran-4-ol

HRID 547041Notes

Reaction equation

HRID 547041 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[CH2:15]([C:17]([C:28]1[CH:33]=[CH:32][C:31]([C:34]#[C:35][C:36]2([OH:42])[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[C:30]([CH3:43])[CH:29]=1)([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([CH3:27])[CH:21]=1)[CH2:18][CH3:19])[CH3:16]>O1CCCC1.[Cl-].[Na+].O.C(OCC)(=O)C>[CH2:15]([C:17]([C:28]1[CH:33]=[CH:32][C:31](/[CH:34]=[CH:35]/[C:36]2([OH:42])[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[C:30]([CH3:43])[CH:29]=1)([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([CH3:27])[CH:21]=1)[CH2:18][CH3:19])[CH3:16]

Participants

6

Reactant 2

HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 577089754-{4-[1-Ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenylethynyl}-tetrahydro-pyran-4-ol

Product 1

HCID 574541474-((E)-2-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl}-vinyl)-tetrahydro-pyran-4-olYield 99.5%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

Sodium bis(2-methoxyethoxy)aluminum hydride (65 wt % solution in toluene, 1.06 mL, 3.516 mmol) was added to a solution of 4-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenylethynyl}-tetrahydro-pyran-4-ol (Example 130-(1); 0.46 g, 1.172 mmol) in tetrahydrofuran (5 mL) in a nitrogen atmosphere at 0° C., and the mixture was stirred at 0° C. for three hours. Then, ethyl acetate and brine were added to the reaction mixture, which was further diluted with ethyl acetate. Thereafter, celite was added and the mixture was stirred at room temperature for three hours. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 30:70, 40 minutes) to give the target compound as a colorless oil (0.46 g, 99%).

Workup

  1. additionThereafter, celite was added
  2. stirringthe mixture was stirred at room temperature for three hours
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 30:70, 40 minutes)

Sources & evidence

ORD record
ord-0a2a822fddc44afe9a4c3b110eeebf20
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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