Diisobutylaluminum hydride → (2E)-3-(4-Methoxy-2-nitrophenyl)prop-2-en-1-ol

HRID 1914696Notes

Reaction equation

HRID 1914696 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](OC)=[O:12])=[C:5]([N+:15]([O-:17])=[O:16])[CH:4]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[CH2:11][OH:12])=[C:5]([N+:15]([O-:17])=[O:16])[CH:4]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 11791213methyl(2E)-3-(4-methoxy-2-nitrophenyl)acrylate

Product 1

HCID 11321750(2E)-3-(4-Methoxy-2-nitrophenyl)prop-2-en-1-olYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of methyl (2E)-3-(4-methoxy-2-nitrophenyl)acrylate (14 g, 0.06 mol) in dry toluene (150 mL) under nitrogen is added dropwise DIBAL-H (63 mL, 0.19 mol, 3 M) at 0° C. After stirring at room temperature for 3 h, the reaction mixture is quenched with MeOH (60 mL) then 1.5 N HCl (60 mL) is added. After addition of another 100 mL of 1.5 N HCl, the product is extracted with EtOAc. The organic layer is washed with water and brine then dried over Na2SO4. The solvent is removed under reduced pressure to afford 10 g (81%) of the title compound as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 7.52-7.54 (m, 1H), 7.43 (s, 1H), 7.11-7.14 (m, 1H), 7.0-7.04 (m, 1H), 6.22-6.29 (m, 1H), 4.35-4.37 (m, 2H), 3.88 (s, 3H).

Workup

  1. customthe reaction mixture is quenched with MeOH (60 mL)
  2. addition1.5 N HCl (60 mL) is added
  3. additionAfter addition of another 100 mL of 1.5 N HCl
  4. extractionthe product is extracted with EtOAc
  5. washThe organic layer is washed with water and brine
  6. dry with materialthen dried over Na2SO4
  7. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-41c050c474ea4a388ba9d1ef3134c04e
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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