2-(5-Bromo-2-methoxyphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole → 2-(5-Bromo-2-(phenethyl)phenyl)-4,4-dimethyl-4,5-dihydrooxazole

HRID 1106794Notes

Reaction equation

HRID 1106794 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](OC)=[C:6]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)[CH:7]=1.[C:17]1([CH2:23][CH2:24][Mg]Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1.C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:24][CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:6]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 128346732-(5-Bromo-2-methoxyphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazoleHCID 178419670HCID 178419670, compound

Product 1

HCID 226755072-(5-Bromo-2-(phenethyl)phenyl)-4,4-dimethyl-4,5-dihydrooxazoleYield 103.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(5-bromo-2-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole (31.21 g) in THF (40 ml) was added PhCH2CH2MgBr (0.22 mol) as a solution in diethyl ether (240 ml). The mixture was stirred for 18 hours, the solvents evaporated and the residue partitioned between ethyl acetate and saturated aqueous ammonium chloride. The organic layer was separated, evaporated and the resulting residue purified by MPLC eluting with dichloromethane to give 2-(5-bromo-2-(phenethyl)phenyl)-4,4-dimethyl-4,5-dihydrooxazole (40.56 g).

Workup

  1. customthe solvents evaporated
  2. customthe residue partitioned between ethyl acetate and saturated aqueous ammonium chloride
  3. customThe organic layer was separated
  4. customevaporated
  5. customthe resulting residue purified by MPLC
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-deb8f7a09e304fea97e93cd563b349ce
Source dataset
uspto-grants-2000_05
Patent number
US06057345

Reaction notes

Loading…