1,10-Phenanthroline → 2-[(1-Hydroxy-1-methylpropyl)]-1,10-phenanthroline

HRID 1581751Notes

Reaction equation

[N:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.[I-].[I-].[Sm+2].[CH2:18]([C:20]([CH3:22])=[O:21])[CH3:19]>O1CCCC1>[OH:21][C:20]([C:2]1[CH:3]=[CH:4][C:5]2[C:14](=[C:13]3[C:8](=[CH:7][CH:6]=2)[CH:9]=[CH:10][CH:11]=[N:12]3)[N:1]=1)([CH3:22])[CH2:18][CH3:19]

Participants

Conditions

Temperature: 25 °C

Procedure

An embodiment of the process comprises mixing a stirred solution of 1,10-phenanthroline in tetrahydrofuran (THF) with a solution of the lanthanideII, samarium diiodide, in THF at a temperature of about 25° C. To the mixed solutions is added a solution of the ketone, methyl ethyl ketone, and the reaction mixture is stirred at about 25° C. for about 12 hours. The reaction is then quenched by the addition of a saturated aqueous solution of ammonium chloride and the mixture extracted with methylene chloride. The extract is washed with brine, dried and concentrated in vacao. The concentrate of product is purified by flash chromatography using alumina and ethyl acetate-hexanes as a gradient to provide racemic 2-[(1-hydroxy-1-methylpropyl)]-1,10-phenanthroline. (Formula 1, R=H, R1=ethyl, R2=methyl) This embodiment is depicted in the following reaction scheme wherein MEK is methyl ethyl ketone.

Workup

customat a temperature of about 25° C
customThe reaction is then quenched by the addition of a saturated aqueous solution of ammonium chloride
extractionthe mixture extracted with methylene chloride
washThe extract is washed with brine
customdried
concentrationconcentrated in vacao
concentrationThe concentrate of product
customis purified by flash chromatography

Sources & evidence

ORD record: ord-5beac8eeb5d94f9496ac71b6a127be55
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06730788B1

Reaction notes

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