Sodium bis(2-methoxyethoxy)aluminiumhydride → HCID 57433080, compound

HRID 546873Notes

Reaction equation

HRID 546873 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[CH2:15]([C:17]([C:35]1[CH:40]=[C:39]([CH3:41])[C:38]([OH:42])=[C:37]([CH3:43])[CH:36]=1)([C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][C:28]([CH2:32][CH3:33])([OH:31])[CH2:29][CH3:30])=[C:22]([CH3:34])[CH:21]=1)[CH2:18][CH3:19])[CH3:16]>O1CCCC1.[Cl-].[Na+].O.C(OCC)(=O)C>[CH2:15]([C:17]([C:35]1[CH:36]=[C:37]([CH3:43])[C:38]([OH:42])=[C:39]([CH3:41])[CH:40]=1)([C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([CH2:29][CH3:30])([OH:31])[CH2:32][CH3:33])=[C:22]([CH3:34])[CH:21]=1)[CH2:18][CH3:19])[CH3:16]

Participants

6

Reactant 2

HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 574434904-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-1-pentynyl)-3-methyl-phenyl]-propyl}-2,6-dimethyl-phenol

Product 1

HCID 57433080HCID 57433080, compoundYield 84.3%

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, 4.2 mL, 13.98 mmol) was added to a solution of 4-{1-ethyl-1-[4-(3-ethyl-3-hydroxy-1-pentynyl)-3-methyl-phenyl]-propyl}-2,6-dimethyl-phenol (Example 38-(3); 1.83 g, 4.66 mmol) in tetrahydrofuran (20 mL) in a nitrogen atmosphere at 0° C., and the mixture was stirred at 0° C. for two 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 one hour. 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 (1.55 g, 84%).

Workup

  1. additionThereafter, celite was added
  2. stirringthe mixture was stirred at room temperature for one hour
  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-3fab6e5ea43a4969a65da4c6fcdc9e1a
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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