benzyl 2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate → benzyl 2-(6-formyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate

HRID 377569Notes

Reaction equation

HRID 377569 reaction equation
[OH:1][CH2:2][C:3]1[O:8][CH2:7][N:6]([C:9]([CH3:21])([CH3:20])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[C:5](=[O:22])[C:4]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH:2]([C:3]1[O:8][CH2:7][N:6]([C:9]([CH3:21])([CH3:20])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[C:5](=[O:22])[C:4]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:1]

Participants

4

Reactant 2

HCID 19354618benzyl 2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoateHCID 178418287HCID 178418287, compound

Product 1

HCID 19354598benzyl 2-(6-formyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoateYield 42.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of benzyl 2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (2.0 g) in dichloromethane was added over 5 minutes to a stirred suspension of pyridinium chlorochromate (0.9 g) in dichloromethane at ambient temperature. After stirring for 1 hour the reaction mixture was diluted with dichloromethane and washed with water. The organic solution was dried (magnesium sulphate) and solvent evaporated under reduced pressure to give benzyl 2-(6-formyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (0.85 g) as an orange gum, NMR (CDCl3) 1.5(s,6H), 5.1(s,2H), 5.3(s,2H), 7.2(bs,5H), 7.3-7.4(m,5H), 9.25(s,1H).

Workup

  1. washwashed with water
  2. dry with materialThe organic solution was dried (magnesium sulphate) and solvent
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c6c4f830695b490eb899eabe395ad6c5
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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