Dichloromethane → N-(2-t-butyl-5-formylphenyl)-2-(9H-xanthen-9-yl)acetamide

HRID 977858Notes

Reaction equation

HRID 977858 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][C:6]=1[NH:13][C:14](=[O:30])[CH2:15][CH:16]1[C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:23][C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(OCC)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][C:6]=1[NH:13][C:14](=[O:30])[CH2:15][CH:16]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=2[O:23][C:24]2[C:29]1=[CH:28][CH:27]=[CH:26][CH:25]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 22078730N-(2-t-butyl-5-hydroxymethylphenyl)-2-(9H-xanthen-9-yl)acetamideHCID 178418287HCID 178418287, compound

Product 1

HCID 19966116N-(2-t-butyl-5-formylphenyl)-2-(9H-xanthen-9-yl)acetamideYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.24 g (3.08 mmol) of N-(2-t-butyl-5-hydroxymethylphenyl)-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 14) were added to 12 ml of a methylene chloride suspension containing 1.06 g (4.92 mmol) of pyridinium chlorochromate. The mixture was then stirred for 1.75 hours. At the end of this time, the reaction suspension was diluted with diethyl ether, filtered through a column using 50 ml of Florisil (trade mark) absorbent, and eluted with a 1:1 by volume mixture of methylene chloride and diethyl ether. The solvent was then removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 50 g of silica gel. Elution with a 1:9 by volume mixture of diethyl ether and methylene chloride afforded the title compound containing a small amount of impurities. Recrystallization of this from a mixture of ethyl acetate and hexane afforded 442 mg of the title compound as crystals, melting at 172.5°-174° C. (after recrystallization from a mixture of ethyl acetate and hexane). The mother liquors were condensed and subjected to column chromatography through 100 g of silica gel. Elution with a 4:6 by volume mixture of ethyl acetate and hexane afforded a further 643 mg of the title compound. The total yield was 88%.

Workup

  1. filtrationfiltered through a column
  2. washeluted with a 1:1 by volume mixture of methylene chloride and diethyl ether
  3. customThe solvent was then removed by distillation under reduced pressure
  4. washElution with a 1:9
  5. additionby volume mixture of diethyl ether and methylene chloride

Sources & evidence

ORD record
ord-a72ef956807f43ed9461f2ab19df7cad
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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