Hexane → HCID 69423031, compound

HRID 349897Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:19][O:20][C:21]1[CH:43]=[CH:42][C:24]([CH2:25][N:26]2[CH:30]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[C:28]([C:37](OCC)=[O:38])=[CH:27]2)=[CH:23][CH:22]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].CCCCCC>O1CCCC1>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:10][C:9]=1[CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:25][N:26]2[CH:30]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[C:28]([CH2:37][OH:38])=[CH:27]2)=[CH:42][CH:43]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminium hydride (0.25 g) was added to a solution of ethyl 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-(2-pyridyl)pyrrole-3-carboxylate (2.40 g) in tetrahydrofuran (30 ml) at 0° C., and the mixture was stirred at 0° C. for 30 minutes. After sodium sulfate decahydrate (2.13 g) and hexane (30 ml) were added to the reaction mixture, the mixture was stirred at room temperature for 30 minutes. After the precipitate was removed by filtration, the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and [1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-(2-pyridyl)-3-pyrrolyl]methanol (2.09 g, yield: 95%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

stirringthe mixture was stirred at room temperature for 30 minutes
customAfter the precipitate was removed by filtration
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-7c5706f830504338b095d525a8ce0598
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179823B1

Reaction notes

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