Water → HCID 178466002, compound

HRID 1368556Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([C:17]1[N:18]=[CH:19][N:20](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:21]=1)([OH:16])[CH:13]([CH3:15])[CH3:14])[CH:6]=[CH:5]2.C([Li])CCC.CN(OC)[C:48](=[O:50])[CH3:49].O>C1COCC1.CCCCCC>[OH:16][C:12]([C:7]1[CH:8]=[C:3]2[C:4](=[CH:5][CH:6]=1)[CH:9]=[C:10]([C:48](=[O:50])[CH3:49])[CH:11]=[CH:2]2)([C:17]1[N:18]=[CH:19][NH:20][CH:21]=1)[CH:13]([CH3:14])[CH3:15]

Participants

Conditions

Temperature: -70 °C

Procedure

1-(6-Bromonaphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (7.0 g) was dissolved in THF (150 ml). The solution was cooled to −70° C. To the mixture was slowly added a solution of n-butyl lithium in hexane (1.6 M; 16.4 ml), and the mixture was stirred at −70° C. for 20 min. To the mixture was added dropwise a solution of N-methyl-N-methoxyacetamide (2.45 g) in THF (10 ml), and the mixture was stirred at −70° C. for 20 min. To the mixture was added water, and the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution and dried. The solvent was distilled off and the residue was purified column chromatography (eluent, hexane:THF=6:1→3:1) to give the titled compound (3.53 g) as a colorless powder.

Workup

stirringthe mixture was stirred at −70° C. for 20 min
extractionthe mixture was extracted with ethyl acetate
washwashed with saturated sodium chloride solution
customdried
distillationThe solvent was distilled off
customthe residue was purified column chromatography (eluent, hexane:THF=6:1→3:1)

Sources & evidence

ORD record: ord-2667ef78a5904bd29faca25e0650d449
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573289B1

Reaction notes

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