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 355757Notes

Reaction equation

HRID 355757 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-42ba806accb540ecbf2e25fb7f266b93
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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