Acetic Acid → Ethyl 2-(4-(benzyloxy)-2-methoxybenzylidene)-3-oxobutanoate

HRID 1617197Notes

Reaction equation

HRID 1617197 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([O:17][CH3:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:25][CH2:26][CH3:27])(=[O:24])[CH2:20][C:21]([CH3:23])=[O:22].C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[C:20]([C:21](=[O:22])[CH3:23])[C:19]([O:25][CH2:26][CH3:27])=[O:24])=[C:11]([O:17][CH3:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 8082Piperidine2×HCID 8868Ethyl AcetoacetateHCID 42939904-Benzyloxy-2-methoxybenzaldehyde

Product 1

HCID 68413560Ethyl 2-(4-(benzyloxy)-2-methoxybenzylidene)-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 4-(benzyloxy)-2-methoxybenzaldehyde (28.3 g), ethyl acetoacetate (18 ml), acetic acid (1.74 ml) and piperidine (0.56 ml) in toluene (400 ml) was heated under reflux for 48 h. A solution of acetic acid (1.74 ml) and piperidine (0.56 ml) in toluene (10 ml) was added and the solution heated under reflux for a further 48 h. The solvent was evaporated under reduced pressure and the residue partitioned between EtOAc and brine. The organics were separated, washed with aq NaHCO3 soln, 1M HCl, brine, dried and evaporated under reduced pressure to give the subtitle compound, 40 g (used crude in next step).

Workup

  1. temperatureunder reflux for 48 h
  2. temperaturethe solution heated
  3. temperatureunder reflux for a further 48 h
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue partitioned between EtOAc and brine
  6. customThe organics were separated
  7. washwashed with aq NaHCO3 soln
  8. dry with material1M HCl, brine, dried
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8c3b35087a9d44139bbd1eeef3e43e1c
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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