3-Methoxybenzaldehyde → HCID 18172428, compound

HRID 397067Notes

Reaction equation

HRID 397067 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[CH2:1]([N:8]([CH2:25][C:24]1[CH:27]=[CH:28][CH:29]=[C:22]([O:21][CH3:20])[CH:23]=1)[CH2:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 115693-MethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 16753664HCID 16753664, compound

Product 1

HCID 18172428HCID 18172428, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-benzylamino-1-(4-methoxy-phenyl)-ethanone (12.0 g, 47.0 mmol, see Preparation 60) and 3-methoxy benzaldehyde (6.09 g, 44.8 mmol) in 1,2 DCE (250 ml) was added NaB(OAc)3H. The reaction mixture was stirred at RT overnight. The reaction was poured into sat. NaHCO3 (150 ml) and extracted with CH2Cl2 (3×100 ml). The combined organics were dried over MgSO4, filtered, and concentrated in vacuo. Flash chromatography (SiO2, gradient elution 20% to 50% EtOAc/hexanes) gave the title product (13.85 g, 36.9 mmol, 83% yield).

Workup

  1. extractionextracted with CH2Cl2 (3×100 ml)
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washFlash chromatography (SiO2, gradient elution 20% to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ed7de7cbbf334ecca63ee1e46dde9a31
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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