Water → HCID 15661749, compound

HRID 1756337Notes

Reaction equation

HRID 1756337 reaction equation
C([O:3][C:4](=O)/[CH:5]=[CH:6]/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[N:10]=1)C.[H-].C([Al+]CC(C)C)C(C)C.C(O)(C)C.O>C1(C)C=CC=CC=1.ClCCl>[Br:15][C:11]1[N:10]=[C:9](/[CH:8]=[CH:7]/[CH:6]=[CH:5]/[CH2:4][OH:3])[CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 15661748HCID 15661748, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 15661749HCID 15661749, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.6 g of 5-(6-bromo-2-pyridyl)-(E,E)-2,4-pentadienoic acid ethyl ester in 73 ml of toluene is mixed with stirring and under argon atmosphere at -70° C. by instillation with 15.4 ml of diisobutylaluminum hydride (20% solution in toluene) and the mixture is stirred for 45 more minutes at this temperature. The reaction mixture is mixed at -70° C. in succession by instillation with 5.5 ml of isopropanol and 7.3 ml of water, stirred for 1 hour at room temperature, suctioned off on diatomaceous earth, rewashed with dichloromethane, the filtrate is dried on sodium sulfate and concentrated by evaporation. 2.2 g of 5-(6-bromo-2-pyridyl)-(E,E)-2,4-pentadien1-ol is obtained as crude product.

Workup

  1. stirringstirred for 1 hour at room temperature
  2. customthe filtrate is dried on sodium sulfate
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-4cfc9edf63da4d8085b035931cff9bb6
Source dataset
uspto-grants-1995_08
Patent number
US05440044

Reaction notes

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