Water → 875708-42-2

HRID 884139Notes

Reaction equation

HRID 884139 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.O.[OH-].[Na+]>C1COCC1>[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][NH2:19])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 11241134HCID 11241134, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 68526000875708-42-2

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride (2.66 g, 70 mmol) in THF (2.00 mL) was added dropwise under ice cooling a solution of 4-(tetrahydropyran-2-yloxy)benzonitrile in THF (70 mL). The resulting solution was then refluxed for 1 hour. The resulting reaction solution was again cooled with ice, and then to the solution was added dropwise, in order, water (2.66 mL), 1 N aqueous sodium hydroxide (2.66 mL) and water (7.98 mL). Insoluble matter was removed by filtration. The filtrate was concentrated under reduced pressure, after which the residue was purified by silica gel column chromatography (chloroform methanol 7:1), to thereby yield 11.41 g of the title compound.

Workup

  1. temperatureThe resulting solution was then refluxed for 1 hour
  2. customThe resulting reaction solution
  3. temperaturewas again cooled with ice
  4. customInsoluble matter was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customafter which the residue was purified by silica gel column chromatography (chloroform methanol 7:1)

Sources & evidence

ORD record
ord-2dbb08e1e4734b52a88c201425b8705b
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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