Acetonitrile → 2-(4-Bromo-phenyl)-5-methyl-4-vinyl-oxazole

HRID 1445768

Reaction equation

HRID 1445768 reaction equation
CN1CCN2CCN(C)P1N(C)CC2.C(#N)C.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:26][C:27]([CH3:33])=[C:28]([CH2:30][CH2:31]I)[N:29]=2)=[CH:21][CH:20]=1>C1COCC1>[Br:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[O:26][C:27]([CH3:33])=[C:28]([CH:30]=[CH2:31])[N:29]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 6342Acetonitrile2×HCID 41867232,8,9-Trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecaneHCID 589513942-(4-Bromo-phenyl)-4-(2-iodo-ethyl)-5-methyl-oxazole2×

Product 1

HCID 222611552-(4-Bromo-phenyl)-5-methyl-4-vinyl-oxazoleYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 2,8,9-trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (3.17 g, 14.7 mmol) as a solution using acetonitrile (10 mL) to a solution of 2-(4-bromo-phenyl)-4-(2-iodo-ethyl)-5-methyl-oxazole (See Intermediate 30) (4.38 g, 11.1 mmol) in 2.8:1 acetonitrile:THF (190 mL). After 4 hrs, concentrate under reduced pressure and add EtOAc and water to the residue. Separate the layers and extract the aqueous material with EtOAc. Wash the crude organic extract with water, dry over MgSO4, filter and concentrate. Purify on silica gel eluting with 7% EtOAc to give 2-(4-bromo-phenyl)-5-methyl-4-vinyl-oxazole (2.31 g, 83%): 1H NMR (400 Hz): (CDCl3) δ 7.89 (d, 2H, J=8 Hz), 7.57 (d, 2H, J=8 Hz), 6.54 (dd, 1H, J=17, 11 Hz), 5.93 (dd, 1H, J=17, 2 Hz), 5.29 (dd, 1H, J=11, 2 Hz), 2.40 (s, 3H).

Workup

  1. concentrationconcentrate under reduced pressure
  2. additionadd EtOAc and water to the residue
  3. customSeparate the layers
  4. extractionextract the aqueous material with EtOAc
  5. washWash the crude
  6. extractionorganic extract with water
  7. dry with materialdry over MgSO4
  8. filtrationfilter
  9. concentrationconcentrate
  10. customPurify on silica gel eluting with 7% EtOAc

Sources & evidence

ORD record
ord-ba4c2a92eedd4af18842cbe06c550aa2
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Linked notes

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