Water → HCID 178450044, compound

HRID 1368550Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Br:12])[CH:8]=2)[CH:3]=1.[CH2:13]([Li])[CH2:14][CH2:15]C.[CH:18]([C:20]1[N:21]=[CH:22][N:23](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:24]=1)=[O:19].O>C1COCC1.CCCCCC>[Br:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([C:18]([C:20]1[N:21]=[CH:22][NH:23][CH:24]=1)([OH:19])[CH:14]([CH3:15])[CH3:13])[CH:11]=[CH:10]2

Participants

Conditions

Temperature: -50 °C

Procedure

2,6-Dibromonaphthalene (25.0 g) was dissolved in THF (1250 ml). The solution was cooled to −50° C. To the solution was slowly added a solution of n-butyllithium in hexane (1.6 M; 57 ml), and the mixture was stirred at −50° C. for 20 min. To the mixture was added dropwise a solution of 4-formyl-1-trityl-1H-imidazole (22.2 g) in THF (200 ml). The mixture was stirred at 50° C. for 20 min. To the mixture was added water, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, dried and concentrated. The residue was purified by silica gel chromatography (eluent, hexane:THF=1:1), and recrystallized from hexane-THF to give the titled compound (31.2 g) as a pale brown powder.

Workup

stirringThe mixture was stirred at 50° C. for 20 min
customthe organic layer was separated
extractionThe aqueous layer was extracted with ethyl acetate
customdried
concentrationconcentrated
customThe residue was purified by silica gel chromatography (eluent, hexane:THF=1:1)
customrecrystallized from hexane-THF

Sources & evidence

ORD record: ord-947abb26948743bda8d5c21d7c41d352
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573289B1

Reaction notes

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