Methanol → 4-Methyl-3-phenylpentanal

HRID 1071618Notes

Reaction equation

HRID 1071618 reaction equation
CN(OC)[C:3](=[O:15])[CH2:4][CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:6]([CH3:8])[CH3:7].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.CO>O1CCCC1>[CH3:7][CH:6]([CH3:8])[CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:4][CH:3]=[O:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 22393573N-Methyl-N-methoxy-4-methyl-3-phenylpentaneamideHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 125985904-Methyl-3-phenylpentanalYield 124.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, N-methyl-N-methoxy-4-methyl-3-phenyl-pentaneamide (215 mg) was dissolved in tetrahydrofuran (9.1 mL) at −78° C., and a diisobutylaluminum hydride/toluene solution (1.5 M, 1.2 mL) was added. After one hour, methanol (3 mL) was added to the reaction system, the temperature of the mixture was returned to room temperature after termination of foaming, and the mixture was continuously stirred. The organic layer was separated by adding diethyl ether, water and a 1N aqueous hydrochloric acid thereto. The resulting organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. After filtering off the drying agent, the mixture was evaporated, to give the title compound as a colorless oil (200 mg). The resulting compound was used for the next reaction without purification.

Workup

  1. customwas returned to room temperature
  2. customThe organic layer was separated
  3. additionby adding diethyl ether, water
  4. washThe resulting organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtering off the drying agent
  7. customthe mixture was evaporated

Sources & evidence

ORD record
ord-6242f59d93574233897e74eac4477b11
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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