Dichloromethane → HCID 11424306, compound

HRID 1654768Notes

Reaction equation

HRID 1654768 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(Cl)Cl.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[C:32][CH:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[OH:34])[CH:26]=1>C(OCC)C>[C:35]1([C:33](=[O:34])[C:32]#[C:31][C:27]2[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2724130Cornforth reagentHCID 11447136HCID 11447136, compound

Product 1

HCID 11424306HCID 11424306, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Place pyridinium dichromate (1.75 g) and methylene chloride (20 mL) under argon atmosphere and cool to 0° C. Add α-[(3-pyridinyl)ethynyl]-benzenemethanol (663 mg, 3.2 mmol)). Stir overnight while slowly warming to room temperature. Dilute with ethyl ether and filter the chromium salts. Purify by silica gel chromatography (2:1 ethyl acetate/hexane) to yield the title compound.

Workup

  1. filtrationfilter the chromium salts
  2. customPurify by silica gel chromatography (2:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-48638178bcfc47868c165987d477ad0e
Source dataset
uspto-grants-1995_04
Patent number
US05409942

Reaction notes

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