Methyl 4-Formylbenzoate → HCID 86750601, compound

HRID 977248Notes

Reaction equation

HRID 977248 reaction equation
[Cl-].[CH3:2][C:3]1[O:7][C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)=[N:5][C:4]=1[CH2:18][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[H-].[Na+].[CH:40]([C:42]1[CH:51]=[CH:50][C:45]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][CH:43]=1)=O>CN(C=O)C>[CH3:2][C:3]1[O:7][C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)=[N:5][C:4]=1/[CH:18]=[CH:40]/[C:42]1[CH:51]=[CH:50][C:45]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 24758Sodium hydrideHCID 19965646HCID 19965646, compound

Product 1

HCID 86750601HCID 86750601, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[5-Methyl-2-(2-naphthyl)-4-oxazolylmethyl]triphenylphosphonium chloride (18.4 g) was suspended in DMF (200 ml), and sodium hydride (60% in oil, 1.42 g) was added little by little at 0° C. After mixture stirring at room temperature for1 hour, methyl 4-formylbenzoate (5.80 g) was added, followed by stirring for 3 hours. The reaction mixture was poured over ice-water; the resulting crystal was collected by filtration. The crystal was then purified by silica gel column chromatography to yield methyl (E)-4-[2-[5-methyl-2-(2-naphthyl)-4-oxazolyl]vinyl]benzoate (10.3 g, 79%) from the fraction eluted with ethyl acetate-chloroform (5:95, v/v), which was then recrystallized from dichloromethane-methanol to yield light yellow prisms having a melting point of 216°-217° C.

Workup

  1. stirringby stirring for 3 hours
  2. filtrationthe resulting crystal was collected by filtration
  3. customThe crystal was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-abc7967d2f6645c48c3bf4fa764a809f
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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