Dichloromethane → HCID 15289378, compound

HRID 1654760Notes

Reaction equation

HRID 1654760 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(Cl)Cl.[CH3:25][N:26]([CH3:43])[C:27]1[CH:32]=[CH:31][C:30]([CH:33]([C:35]#[C:36][C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)[OH:34])=[CH:29][CH:28]=1.CN(C)C1C=CC(C(C#C)O)=CC=1>C(OCC)C>[CH3:43][N:26]([CH3:25])[C:27]1[CH:28]=[CH:29][C:30]([C:33](=[O:34])[C:35]#[C:36][C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 2724130Cornforth reagentHCID 2749588HCID 2749588, compoundHCID 15289377HCID 15289377, compound

Product 1

HCID 15289378HCID 15289378, 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 a 1:1 mixture of 4-dimethylamino-α-[(4-pyridinyl)ethynyl]-benzenemethanol and 4-dimethylamino-α-(ethynyl)benzenemethanol (0.8 g). 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 0.94 g of the title compound; mp 143°-145° C.

Workup

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

Sources & evidence

ORD record
ord-b230ce98031144468072198e0ea88640
Source dataset
uspto-grants-1995_04
Patent number
US05409942

Reaction notes

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