Water → HCID 23130698, compound

HRID 2080129Notes

Reaction equation

HRID 2080129 reaction equation
[CH3:1][C:2]([CH3:14])=[CH:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]([CH3:14])=[CH:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9][NH2:10]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23130686HCID 23130686, compound

Product 1

HCID 23130698HCID 23130698, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(3-Methyl-2-butenyloxy)-benzonitrile described in Preparation Example 133 (1.71 g, 10 mmol) was dissolved in tetrahydrofuran (20 mL), lithium aluminum hydride (0.57 g, 15 mmol) was added under stirring at room temperature, the solution was heated to 70° C., then stirring continued for 2 hours. The reaction solution was cooled on an ice bath, then, water (0.6 mL), an aqueous solution of 15% sodium hydroxide (0.6 mL) and water (1.8 mL) were added in this order, then, the solid was filtered, and washed with tetrahydrofuran (20 mL). The filtrate and the washings were combined, and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo, and the title compound (1.50 g, 8.52 mmol, 85.2%) was obtained as a colorless oil.

Workup

  1. temperaturethe solution was heated to 70° C.
  2. stirringstirring
  3. temperatureThe reaction solution was cooled on an ice bath
  4. filtrationthe solid was filtered
  5. washwashed with tetrahydrofuran (20 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-890b540f9b4040d4aa11a0cc7ceaa950
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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