Sodium Chloride → HCID 68718678, compound

HRID 1171223Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12]([C:14]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=O)=[CH:11][C:10]=2[CH:23]=1.O.NN.[OH-].[K+].[Na+].[Cl-]>C(O)CO>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12]([CH2:14][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[CH:11][C:10]=2[CH:23]=1

Participants

Conditions

Temperature: 10 °C

Procedure

To an ethylene glycol (5 mL) suspension of (5-[1,3]-dioxolan-2-yl-benzofuran-2-yl)-(4-fluoro-phenyl)-methanone (370 mg, 1.18 mmol) were added hydrazine monohydrate (165 mg, 2.8 mmol) and potassium hydroxide (152 mg, 2.71 mmol). After stirring this suspension for 2 hours at 10° C., this suspension was further stirred for 1 hour at 160° C. After allowing the reaction mixture to cool on standing, sat. NaCl was poured thereinto followed by extraction with ethyl acetate. The organic layer was separated followed by drying over anhydrous magnesium sulfate and concentrating under a reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 5-[1,3]-dioxolan-2-yl-2-(4-fluoro-benzyl)-benzofuran (151 mg, 43%).

Workup

stirringthis suspension was further stirred for 1 hour at 160° C
temperatureto cool
extractionthereinto followed by extraction with ethyl acetate
customThe organic layer was separated
dry with materialby drying over anhydrous magnesium sulfate
concentrationconcentrating under a reduced pressure
customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-598e3c0a3cf648929cd5985dc537dec1
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829585B2

Reaction notes

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