Hydrochloric Acid → 3-(5-Butylthiophen-2-yl)-5-(4-octylphenyl)-isoxazole

HRID 1167045Notes

Reaction equation

[CH2:1]([C:5]1[S:9][C:8]([C:10](=[N:12][OH:13])[CH3:11])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].C([Li])CCC.[CH2:19]([C:27]1[CH:36]=[CH:35][C:30]([C:31](OC)=O)=[CH:29][CH:28]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].Cl>O1CCCC1>[CH2:1]([C:5]1[S:9][C:8]([C:10]2[CH:11]=[C:31]([C:30]3[CH:35]=[CH:36][C:27]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:28][CH:29]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

The 1-(5-butylthiophen-2-yl)-ethanone oxime obtained in step 2 is dissolved in tetrahydrofuran under an inert gas atmosphere and doubly deprotonated with 2 equivalents of n-butyllithium at 0° C. The solution is admixed with a solution of 0.5 equivalents of methyl 4-octylbenzoate in tetrahydrofuran, and the mixture is stirred for 30 min at 0° C., then admixed with 3 M HCl and refluxed for 1 h. Customary work-up followed by purification by column chromatography over silica gel 60 (eluent: dichloromethane/heptane 1:1) and recrystallizsation affords 3-(5-butylthiophen-2-yl)-5-(4-octylphenyl)-isoxazole; X 63 SC 82 SA 88 N 89 I.

Workup

temperaturerefluxed for 1 h
customCustomary work-up followed by purification by column chromatography over silica gel 60 (eluent: dichloromethane/heptane 1:1) and recrystallizsation

Sources & evidence

ORD record: ord-86a97f62f4474ff9af2a5a097f1a91fb
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06616989B1

Reaction notes

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