Boron tribromide → Ethyl [3-[[2-(4,5-diphenyloxazol-2-yl)-1-cyclopenten-1-yl]methyl]phenoxy]acetate

HRID 377326Notes

Reaction equation

HRID 377326 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH2:22][CH2:21][CH2:20][C:19]=3[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C2N=C(C3C(CC4C=C[CH:58]=[C:57]([O:61][CH3:62])C=4)CCC=3)OC=2C2C=CC=CC=2)C=CC=CC=1.B(Br)(Br)Br.C1(C2N=C(C3CCCC=3CC3C=CC=C(O)C=3)[O:76]C=2C2C=CC=CC=2)C=CC=CC=1.C1(C2N=C(C3C(CC4C=CC=C(O)C=4)CCC=3)OC=2C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.C(OCC)(=O)C>[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH2:22][CH2:21][CH2:20][C:19]=3[CH2:23][C:24]3[CH:25]=[C:26]([CH:27]=[CH:28][CH:29]=3)[O:30][CH2:31][C:62]([O:61][CH2:57][CH3:58])=[O:76])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 25134Boron tribromideHCID 193584211-(4,5-Diphenyloxazol-2-yl)-2-(3-hydroxybenzyl)cyclopenteneHCID 193584311-(4,5-Diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclopenteneHCID 211964711-(4,5-Diphenyloxazol-2-yl)-5-(3-hydroxybenzyl)-cyclopenteneHCID 211965411-(4,5-Diphenyloxazol-2-yl)-5-(3-methoxybenzyl)cyclopentene

Product 1

HCID 54031249Ethyl [3-[[2-(4,5-diphenyloxazol-2-yl)-1-cyclopenten-1-yl]methyl]phenoxy]acetate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of a mixture of 1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclopentene and 1-(4,5-diphenyloxazol-2-yl)-5-(3-methoxybenzyl)cyclopentene (2 g) in methylene chloride (30 ml) was added boron tribromide in methylene chloride (1M, 9.8 ml) at 0C. After being stirred for 2 hours at 0° C., the solvent was evaporated in vacuo to give a residue containing a mixture of 1-(4,5-diphenyloxazol-2-yl)-2-(3-hydroxybenzyl)cyclopentene and 1-(4,5-diphenyloxazol-2-yl)-5-(3-hydroxybenzyl)-cyclopentene. The residue was diluted with ethyl acetate and the solution was washed with water and brine. The dried solvent was evaporated in vacuo. The oily residue was dissolved in N,N-dimethylformamide (20 ml). To the solution were added potassium carbonate (2.0 g) and ethyl bromoacetate (2.2 ml), and the resulting mixture was stirred for 3 hours at room temperature. The reaction solution was partitioned between ethyl acetate and water and the organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was chromatographed on silica gel using n-hexane--ethyl acetate as an eluent. The first fraction gave ethyl [3-[[2-(4,5-diphenyloxazol-2-yl)-1-cyclopenten-1-yl]methyl]phenoxy]acetate (0.38 g).

Workup

  1. customthe solvent was evaporated in vacuo
  2. customto give a residue
  3. additioncontaining
  4. washthe solution was washed with water and brine
  5. customThe dried solvent was evaporated in vacuo
  6. dissolutionThe oily residue was dissolved in N,N-dimethylformamide (20 ml)
  7. additionTo the solution were added potassium carbonate (2.0 g) and ethyl bromoacetate (2.2 ml)
  8. stirringthe resulting mixture was stirred for 3 hours at room temperature
  9. customThe reaction solution was partitioned between ethyl acetate and water
  10. washthe organic layer was washed with water and brine
  11. dry with materialdried over magnesium sulfate
  12. customevaporated in vacuo
  13. customThe oily residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-a5270156df7a4dd182c6144d0ee25d7a
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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