Water → 4-{4-[6-(Allyloxy)hexyl]phenyl}-7-phenyl-1,10-phenanthroline

HRID 432549Notes

Reaction equation

[H-].[Na+].[C:3]1([C:9]2[C:10]3[C:19]([N:20]=[CH:21][CH:22]=2)=[C:18]2[C:13]([C:14]([C:23]4[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35])=[CH:25][CH:24]=4)=[CH:15][CH:16]=[N:17]2)=[CH:12][CH:11]=3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:36](Br)[CH:37]=[CH2:38].O>CN(C=O)C.C(OCC)(=O)C>[CH2:38]([O:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][C:26]1[CH:25]=[CH:24][C:23]([C:14]2[C:13]3[C:18](=[C:19]4[C:10](=[CH:11][CH:12]=3)[C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[CH:22][CH:21]=[N:20]4)[N:17]=[CH:16][CH:15]=2)=[CH:28][CH:27]=1)[CH:37]=[CH2:36]

Participants

Conditions

Temperature: 35 °C

Procedure

A 60% dispersion of NaH in mineral oil (76.1 mg) is suspended in DMF (10 ml). To this suspension is added 6-[4-(7-phenyl-1,10-phenanthrolin-4-yl)phenyl]hexan-1-ol (657 mg) followed by mixing at room temperature for 3 hrs. Allyl bromide (242 mg) is then added and the mixture is stirred at 35° C. for 24 hours, or until the reaction is judged complete by TLC. Excess NaH is carefully reacted with water and the reaction mixture is then diluted with ethyl acetate. The organic layer is washed with aqueous 6 M NaCl, dried over MgSO4, concentrated by roto-evaporation, and purified by column chromatography on silica gel to give the desired product.

Workup

additionby mixing at room temperature for 3 hrs
washThe organic layer is washed with aqueous 6 M NaCl
dry with materialdried over MgSO4
concentrationconcentrated by roto-evaporation
custompurified by column chromatography on silica gel

Sources & evidence

ORD record: ord-61c5e826bf2346e197f3507d346fa50c
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06664111B2

Reaction notes

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