Diethyl Ether → HCID 21223275, compound

HRID 1939143Notes

Reaction equation

HRID 1939143 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][CH2:13][C:14]1[O:19][CH2:18][N:17]([C:20]([CH3:28])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:21])[C:16](=[O:29])[C:15]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CCOCC>ClCCl>[CH:13]([C:14]1[O:19][CH2:18][N:17]([C:20]([CH3:28])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:21])[C:16](=[O:29])[C:15]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:12]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21223285HCID 21223285, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 21223275HCID 21223275, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium chlorochromate (4.70 g) was suspended in dichloromethane (20 ml), and a dichloromethane solution (27 ml) of 6-hydroxymethyl-3-(1-methyl-1-phenylethyl)-5-phenyl-2,3-dihydro-4H-1,3-oxazin-4-one (Compound No. 53, 4.70 g) was added thereto at room temperature. After stirring for about 9 hours, a large amount of ether was added and separated by decantation. The organic layer was dried with magnesium sulfate and the solvent was evaporated. The crude product was purified by silica gel chromatography to afford the captioned compound (4.47 g, yield 96%).

Workup

  1. customat room temperature
  2. customseparated by decantation
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-31df65bbf3e54447a5c4265f3cddb28f
Source dataset
uspto-grants-1997_12
Patent number
US05696054

Reaction notes

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