Ethyl Acetate → HCID 18475877, compound

HRID 2187866Notes

Reaction equation

HRID 2187866 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:23][O:24][C:25]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:26]=1[CH:27]=O.CCOC(C)=O>ClCCCl>[CH3:23][O:24][C:25]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:26]=1[CH2:27][NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([OH:1])[CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 115683-AminophenolHCID 691752,4-DimethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18475877HCID 18475877, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3-hydroxyaniline (1 equiv) in 1,2-dichloroethane is added 4Å powdered molecular sieves, followed by sodium triacetoxyborohydride (1.5 equiv). 2,4-dimethoxybenzaldehyde (1.1 equiv) is added, and the reaction is stirred at room temperature. After completion, the reaction is poured into EtOAc, washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the titled product.

Workup

  1. washwashed with sat. aq. NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-743bafe5c2f04035b28c78708d957b4c
Source dataset
uspto-grants-2002_06
Patent number
US06410534B1

Reaction notes

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