Water → HCID 14835699, compound

HRID 1709253Notes

Reaction equation

HRID 1709253 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:16]=[CH:17]/[C:18](OCC)=[O:19])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.[H-].C([Al+]CC(C)C)C(C)C.O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:16]=[CH:17]/[CH2:18][OH:19])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14835698HCID 14835698, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14835699HCID 14835699, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2.99 g of ethyl (E)-3-[3-methoxy-4-(3-pyridyloxy)phenyl]acrylate was dissolved in 30 ml of anhydrous toluene. To the solution was dropwise added 22.0 ml of a 1M toluene solution of diisobutylaluminum hydride at -50° C. in a nitrogen atmosphere. The mixture was stirred for 30 minutes at the same temperature. To the reaction mixture was dropwise added 1.6 ml of water. The mixture was stirred for 1 hour at room temperature. The resulting insolubles were removed by filtration. The filtrate was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 2.57 g of colorless oily (E)-3-[3-methoxy-4-(3-pyridyloxy)phenyl]allyl alcohol.

Workup

  1. customat -50° C.
  2. stirringThe mixture was stirred for 1 hour at room temperature
  3. customThe resulting insolubles were removed by filtration
  4. dry with materialThe filtrate was dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-e1a24adf7a5740c6b054d91051a6fa13
Source dataset
uspto-grants-1990_08
Patent number
US04948796

Reaction notes

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