Methyl 4-(5-cyano-7-isopropenyl-1,3-benzoxazol-2-yl)benzoate → Methyl 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoate

HRID 2066830Notes

Reaction equation

HRID 2066830 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:22]([CH3:24])=[CH2:23])[C:6]2[O:10][C:9]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:21]=1)#[N:2].[H][H]>[Pd].O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:22]([CH3:24])[CH3:23])[C:6]2[O:10][C:9]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:21]=1)#[N:2]

Participants

5

Reactant 2

HCID 68409145Methyl 4-(5-cyano-7-isopropenyl-1,3-benzoxazol-2-yl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 68408018Methyl 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoateYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a 5-gallon reaction vessel was added methyl 4-(5-cyano-7-isopropenyl-1,3-benzoxazol-2-yl)benzoate (40.6 g, Step A), tetrahydrofuran (4 l), and 10% palladium on carbon (8 g). The reaction mixture was heated to 60° C. under 10 psi of hydrogen for 3 h, and then filtered through Celite, washing generously with dichloromethane. Concentration of the eluent in vacuo provided 40.5 g (99%) of the title compound. Mass spectrum (ESI) 321.1 (M+).

Workup

  1. customTo a 5-gallon reaction vessel
  2. filtrationfiltered through Celite
  3. washwashing generously with dichloromethane

Sources & evidence

ORD record
ord-e11bc9f306464ce3b7973bebfc872c1e
Source dataset
uspto-grants-2012_10
Patent number
US08293721B2

Reaction notes

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