Water → HCID 178450084, compound

HRID 1368548

Reaction equation

BrC1C=CC2C(=CC=C(OCF)C=2)C=1.[F:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([C:28]([C:33]1[N:34]=[CH:35][N:36](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:37]=1)([OH:32])[CH:29]([CH3:31])[CH3:30])[CH:22]=[CH:21]2.C([Li])CCC.C(C1N=CN(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=1)=O.O>CCOCC.CCCCCC.C1COCC1>[F:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([C:28]([C:33]1[N:34]=[CH:35][NH:36][CH:37]=1)([OH:32])[CH:29]([CH3:31])[CH3:30])[CH:22]=[CH:21]2

Participants

Conditions

Temperature: -70 °C

Procedure

Production of 1-(6-Fluoromethyloxynaphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol 2-Bromo-6-fluoromethyloxynaphthalene (2.10 g) was dissolved in ether (100 ml), and the solution was cooled to −70° C. To the solution was slowly added a solution of n-butyllithium in hexane (1.6 M, 5.7 ml), and the mixture was stirred at −70° C. for 20 min. To the mixture was added dropwise a solution of 4-formyl-1-trityl-1H-imidazole (1.58 g) in THF (10 ml). The mixture was stirred for 20 min at −70° C. To the mixture was added water, and the mixture was extracted with ethyl acetate and dried. The solvent was distilled off and the residue was purified by silica gel chromatography (eluent, hexane:ethyl acetate=1:1) followed by recrystallization from diisopropyl ether to give the titled compound (1.73 g) as colorless needles.

Workup

stirringThe mixture was stirred for 20 min at −70° C
extractionthe mixture was extracted with ethyl acetate
customdried
distillationThe solvent was distilled off
customthe residue was purified by silica gel chromatography (eluent, hexane:ethyl acetate=1:1)
customfollowed by recrystallization from diisopropyl ether

Sources & evidence

ORD record: ord-3393665c27394134946795a64bd73413
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573289B1

Linked notes

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