Tetrahydrofuran → 2-(3-(Benzyloxy)phenyl)-2-methylpropanal

HRID 1660073Notes

Reaction equation

HRID 1660073 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH3:19])([CH3:18])[C:16]#N)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.[O:30]1CCCC1>CCCCCC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH3:19])([CH3:18])[CH:16]=[O:30])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 204968632-[3-(Benzyloxy)phenyl]-2-methylpropanenitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 198553592-(3-(Benzyloxy)phenyl)-2-methylpropanalYield 99%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a 15° C. solution of 325 g. (1.25 mole of 2-(3-benzyloxyphenyl)-2-methylpropionitrile in 1.85 liters of tetrahydrofuran was added 1.6 moles of diisobutylaluminum hydride as a 1.3 M solution in hexane (reaction temperature is maintained at 15°-18° C.). The reaction mixture was allowed to warm to room temperature and was stirred 2 hours longer. It was then quenched by addition to a solution of 170 ml. of concentrated sulfuric acid in 670 ml. of water (temperature ≤30° C.). The resultant mixture was allowed to warm to room temperature and was then stirred an additional 2 hours. The organic layer was separated and the aqueous phase extracted once with one liter of ether. The combined organic phase was washed with 500 ml. of water and 500 ml. of saturated sodium chloride, dried over magnesium sulfate and evaporated to yield 315 g. (99%) of the title product.

Workup

  1. customTo a 15° C.
  2. customIt was then quenched by addition to a solution of 170 ml
  3. customof water (temperature ≤30° C.)
  4. temperatureto warm to room temperature
  5. stirringwas then stirred an additional 2 hours
  6. customThe organic layer was separated
  7. extractionthe aqueous phase extracted once with one liter of ether
  8. washThe combined organic phase was washed with 500 ml
  9. dry with materialof saturated sodium chloride, dried over magnesium sulfate
  10. customevaporated
  11. customto yield 315 g

Sources & evidence

ORD record
ord-0d42a0c34703402b9da9d28d063df6c9
Source dataset
uspto-grants-1981_12
Patent number
US04306097

Reaction notes

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