4-Pentenal → 1,8-Nonadien-5-ol

HRID 16225

Reaction equation

HRID 16225 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH:3]=[CH2:4].[CH:7](=[O:12])[CH2:8][CH2:9][CH:10]=[CH2:11]>O1CCCC1>[CH2:4]=[CH:3][CH2:2][CH2:1][CH:7]([OH:12])[CH2:8][CH2:9][CH:10]=[CH2:11]

Participants

4

Reactant 2

HCID 164184-PentenalHCID 178418797HCID 178418797, compound

Product 1

HCID 118295421,8-Nonadien-5-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Butenyl-magnesium bromide (125 mL, 0.5 M in tetrahydrofuran, 62.5 mmol) was added drop wise to a stirred and cooled (−78° C.) solution of pent-4-enal (4 g, 48.07 mmol) in dry tetrahydrofuran (160 mL). After the addition, the solution was warmed to room temperature and then quenched with NH4Cl solution. The mixture was partitioned with diethyl ether and the organic phase was washed with brine, dried (MgSO4), filtered, and evaporated. The residue was purified over silica gel using 5-15% diethyl ether in hexanes to give the title compound as an oil.

Workup

  1. additionAfter the addition
  2. customquenched with NH4Cl solution
  3. customThe mixture was partitioned with diethyl ether
  4. washthe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified over silica gel using 5-15% diethyl ether in hexanes

Sources & evidence

ORD record
ord-e98f6149fafa44c789cdbd4327d485dc
Source dataset
uspto-grants-2010_06
Patent number
US07737137B2

Linked notes

Loading…