3-Methoxy-2-methoxymethoxy-5-(2-oxo-oxazolidin-3-yl)benzaldehyde → 3-(3-Methoxy-4-methoxymethoxy-5-methylphenyl)oxazolidin-2-one
Reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:17][CH2:18][O:19][CH3:20])=[C:5]([CH:8]=[C:9]([N:11]2[CH2:15][CH2:14][O:13][C:12]2=[O:16])[CH:10]=1)[CH:6]=O>C(O)(=O)C.C(O)C.[C].[Pd]>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N:11]2[CH2:15][CH2:14][O:13][C:12]2=[O:16])[CH:8]=[C:5]([CH3:6])[C:4]=1[O:17][CH2:18][O:19][CH3:20]Participants
Procedure
3-Methoxy-2-methoxymethoxy-5-(2-oxo-oxazolidin-3-yl)benzaldehyde (0.5 g, 1.79 mmol) was dissolved in a solvent mixture of acetic acid (5 ml) and ethanol (5 ml) and 10% palladium carbon (0.05 g) was added thereto to perform catalytic reduction at 1 atm at 50° C. for 4 hours. The reaction mixture was cooled to room temperature and filtrated by cerite. The filtrate was concentrated under reduced pressure. The residue was dissolved in acetic acid (10 ml) and 10% palladium carbon (0.05 g) was added thereto to perform catalytic reduction at 1 atm at 50° C. for 6 hours. The solvent was removed under reduced pressure to obtain 3-(3-methoxy-4-methoxymethoxy-5-methylphenyl)oxazolidin-2-one as a crude product, which was subjected to the next reaction as it was.
Workup
- additionwas added
- customat 50° C.
- customfor 4 hours
- filtrationfiltrated by cerite
- concentrationThe filtrate was concentrated under reduced pressure
- dissolutionThe residue was dissolved in acetic acid (10 ml)
- addition10% palladium carbon (0.05 g) was added
- customat 50° C.
- customfor 6 hours
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-aa77d31e260040ff9924ee1a7a8fb23a
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071600B2
Reaction notes
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