Dichloromethane → 1-Phenyl-3-(2-furanyl)-2-propyne-1-one

HRID 1654777Notes

Reaction equation

HRID 1654777 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(Cl)Cl.[O:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30]#[C:31][CH:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[OH:33]>C(OCC)C>[C:34]1([C:32](=[O:33])[C:31]#[C:30][C:26]2[O:25][CH:29]=[CH:28][CH:27]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2724130Cornforth reagentHCID 20076917alpha-[(2-Furanyl)ethynyl]-benzenemethanol

Product 1

HCID 144017341-Phenyl-3-(2-furanyl)-2-propyne-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Place pyridinium dichromate (0.75 g, 2 mmol) and methylene chloride (15 mL) under argon atmosphere and cool to 0° C. Add α-[(2-furanyl)ethynyl]-benzenemethanol (297 mg, 1.5 mmol). Stir overnight while slowly warming to room temperature. Dilute with ethyl ether and filter the chromium salts. Purify by silica gel chromatography to give the title compound.

Workup

  1. filtrationfilter the chromium salts
  2. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-a42f66b7f987487399e9614f7813cf37
Source dataset
uspto-grants-1995_04
Patent number
US05409942

Reaction notes

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