Sodium sulfate decahydrate → HCID 117759702, compound

HRID 1049609Notes

Reaction equation

HRID 1049609 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[CH:18][C:17]=1[C:32](=[O:38])[C:33]([CH3:37])([CH3:36])[CH2:34][CH3:35].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[CH:18][C:17]=1[CH:32]([OH:38])[C:33]([CH3:37])([CH3:36])[CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 117759682HCID 117759682, compound

Product 1

HCID 117759702HCID 117759702, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, to a suspension of lithium aluminum hydride (28.2 mg) in THF (5.7 mL) was added dropwise a solution of 1-(2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)-[1,1′-biphenyl]-2-yl)-2,2-dimethylbutan-1-one (162.2 mg) in THF (1.9 mL) at 0° C., and the mixture was stirred for 10 min. To the reaction mixture was added a small portion of sodium sulfate decahydrate at 0° C., and the mixture was filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (155 mg) as a colorless oil.

Workup

  1. filtrationthe mixture was filtered
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a4fffa68ec9a47acbc8c012b4d3c368a
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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