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Water → 3-{[2-(4,5-Diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}-2-methylphenol

HRID 1067134
Notes
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Reaction equation

HRID 1067134 reaction equation
C[O:2][C:3]1[C:4]([CH3:33])=[C:5]([CH:30]=[CH:31][CH:32]=1)[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH:9]=[C:8]1[C:13]1[O:14][C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1.B(Br)(Br)Br.O>C(Cl)Cl>[C:18]1([C:16]2[N:17]=[C:13]([C:8]3[CH:7]([CH2:6][C:5]4[C:4]([CH3:33])=[C:3]([OH:2])[CH:32]=[CH:31][CH:30]=4)[CH2:12][CH2:11][CH2:10][CH:9]=3)[O:14][C:15]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 183673122-[1-(3-Methoxy-2-methylbenzyl)-2-cyclohexen-2-yl]-4,5-diphenyloxazole

Product 1

HCID 183674223-{[2-(4,5-Diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}-2-methylphenolYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 2-[1-(3-methoxy-2-methylbenzyl)-2-cyclohexen-2-yl]-4,5-diphenyloxazole (1.16 g) in CH2Cl2 (25 ml) was added boron tribromide (1M solution in CH2Cl2, 5.32 ml) at −60° C. and the mixture was warmed to 5° C. After stirring for 1 hour at the same temperature, the reaction mixture was stirred for further 1 hour at room temperature. To the mixture was added water under ice-cooling, extracted with EtOAc. The organic layer was washed with water, saturated sodium hydrogen carbonate, water, and brine, dried over magnesium sulfate, evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 5:1) to give 3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}-2-methylphenol (903.8 mg) as an amorphous solid.

Workup

  1. stirringthe reaction mixture was stirred for further 1 hour at room temperature
  2. temperaturecooling
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water, saturated sodium hydrogen carbonate, water, and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 5:1)

Sources & evidence

ORD record
ord-dccc98888f3d4257b7b2609004fae252
Source dataset
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06245790B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes