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

HRID 547057Notes

Reaction equation

HRID 547057 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][S: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][S: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 577091764-{4-[1-Ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenylethynyl}-tetrahydro-thiopyran-4-ol

Product 1

HCID 577090144-((E)-2-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl}-vinyl)-tetrahydro-thiopyran-4-olYield 93.7%

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, 1.2 mL, 4 mmol) was added to a solution of 4-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenylethynyl}-tetrahydro-thiopyran-4-ol (Example 136-(1); 0.54 g, 1.3 mmol) in tetrahydrofuran (6 mL) in a nitrogen atmosphere at 0° C., and the mixture was stirred at 0° C. for five 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 30 minutes. 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 25:75) to give the target compound as a colorless oil (0.5 g, 92%).

Workup

  1. additionThereafter, celite was added
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  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 25:75)

Sources & evidence

ORD record
ord-014b76e17d8e49f1b11e8f9a1747cc1e
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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