Water → HCID 69556315, compound

HRID 428907Notes

Reaction equation

HRID 428907 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](/[C:10](/[CH2:17][CH3:18])=[CH:11]/[C:12](OCC)=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].C([Al+]CC(C)C)C(C)C.O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6](/[C:10](/[CH2:17][CH3:18])=[CH:11]/[CH2:12][OH:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 21225700DiisobutylaluminumhydrideHCID 86585321HCID 86585321, compound

Product 1

HCID 69556315HCID 69556315, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl (E)-3-(3-nitrophenyl)-2-pentenoate (Preparation 13, 105 g, 0.43 mol) in toluene (1400 ml) at −10° C. under nitrogen was added dropwise over 3 h diisobutylaluminium hydride (1.0 M in toluene, 1 l, 1.0 mol), then the mixture was stirred at 0° C. for 1 hour. Water (400 ml) was carefully added, followed by sodium hydrogen carbonate (700 g). The resulting slurry was vigorously stirred for 10 minutes, then ethyl acetate (2 l) was added, and the mixture stirred for 1 h. The mixture was dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a pale brown oil (80 g, 90%).

Workup

  1. stirringThe resulting slurry was vigorously stirred for 10 minutes
  2. stirringthe mixture stirred for 1 h
  3. dry with materialThe mixture was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6c1afcb6baf4522b1b9c085f0a00ff2
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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