Water → 4,4-Diphenyl-2-cyclopentenyl azide

HRID 1657270Notes

Reaction equation

HRID 1657270 reaction equation
C(O[CH:5]1[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH:7]=[CH:6]1)(=O)C.[N-:22]=[N+:23]=[N-:24].[Na+].O1CCCC1.O>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].C(OCC)(=O)C>[C:10]1([C:9]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:8][CH:7]([N:22]=[N+:23]=[N-:24])[CH:6]=[CH:5]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 33557Sodium AzideHCID 100163975,5-Diphenyl-2-cyclopentenyl acetate

Product 1

HCID 103552994,4-Diphenyl-2-cyclopentenyl azideYield 56.8%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5,5-diphenyl-2-cyclopentenyl acetate (0.30 g) and sodium azide (84 mg) in a solution of tetrahydrofuran (3 ml) and water (1.5 ml) was added tetrakis(triphenylphosphine)palladium(O) (62 mg) at room temperature under an argon atmosphere. After being stirred for 14.5 hours, ethyl acetate was added. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of n-hexane and ethyl acetate as an eluent to give 4,4-diphenyl-2-cyclopentenyl azide (0.16 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel with a mixture of n-hexane and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-75abeceedbb0488aa78b37ad51ea58cd
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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