5-phenyl-4-pentyn-1-ol → 4-Pentynal, 5-phenyl-

HRID 1722217Notes

Reaction equation

HRID 1722217 reaction equation
[C:1]1([C:7]#[C:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[C:1]1([C:7]#[C:8][CH2:9][CH2:10][CH:11]=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 111374345-phenyl-4-pentyn-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 112406334-Pentynal, 5-phenyl-

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-phenylpent-4-yn-1-ol (250 mg) in dry CH2Cl2 (2 ml) was added to a suspension of pyridinium chlorochromate (520 mg) in dry CH2Cl2 (3 ml). The mixture was stirred for 2.5 hours and diluted with ether, and the organic solution was decanted off. The oily residue was treated with ether (5×20 ml) and the extracts were washed successively with 5% NaHCO3, water and brine. After drying, the solvent was removed to yield 5-phenylpent-4-ynal.

Workup

  1. customthe organic solution was decanted off
  2. additionThe oily residue was treated with ether (5×20 ml)
  3. washthe extracts were washed successively with 5% NaHCO3, water and brine
  4. customAfter drying
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-417280dbb81b4e1cb4f39d4744db33db
Source dataset
uspto-grants-1989_08
Patent number
US04855086

Reaction notes

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