Propargyl alcohol → 3-Hydroxy-1-[4-chloro-2-benzoylphenyl]propyne

HRID 1701818Notes

Reaction equation

HRID 1701818 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:22]=[CH:23][C:24](I)=[C:25]([CH:34]=1)[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27].[CH2:36]([OH:39])[C:37]#[CH:38]>[Pd](Cl)Cl.C(NCC)C>[OH:39][CH2:36][C:37]#[C:38][C:24]1[CH:23]=[CH:22][C:21]([Cl:20])=[CH:34][C:25]=1[C:26](=[O:27])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 7859Propargyl alcoholHCID 11776TriphenylphosphineHCID 129482625-Chloro-2-iodobenzophenone

Product 1

HCID 128416443-Hydroxy-1-[4-chloro-2-benzoylphenyl]propyne

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 8021DiethylamineSolvent

Procedure

A mixture of 0.17 g (1.0 mmole) of palladium chloride, 0.5 g (2.0 mmole) of triphenylphosphine, 0.1 g (0.5 mmole) of cuprous iodide, 15 g (43 mmole) of 5-chloro-2-iodobenzophenone and 60 ml of diethylamine was stirred at room temperature for 20 min. In one portion 6.0 g (107 mmole) of propargyl alcohol was added, and the resulting mixture was stirred for 24 hr. The solvent was removed at reduced pressure and the residue was dissolved in ether. The ether solution was washed with water, dried with anhydrous sodium sulfate, and concentrated at reduced pressure to give the product as a red oil.

Workup

  1. stirringthe resulting mixture was stirred for 24 hr
  2. customThe solvent was removed at reduced pressure
  3. dissolutionthe residue was dissolved in ether
  4. washThe ether solution was washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-ed133d85e14f488683e8db2ba00900e8
Source dataset
uspto-grants-1983_04
Patent number
US04379090

Reaction notes

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