Water → 2-(1-Bromocyclohexyl)-8-cyanomethyl-4-oxo-4H-[1]-benzopyran

HRID 1200185Notes

Reaction equation

[Br:1][C:2]1([C:8]2[O:9][C:10]3[C:18]([CH2:19]Br)=[CH:17][CH:16]=[CH:15][C:11]=3[C:12](=[O:14])[CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C-:21]#[N:22].[Na+].O>CN(C)C=O>[Br:1][C:2]1([C:8]2[O:9][C:10]3[C:18]([CH2:19][C:21]#[N:22])=[CH:17][CH:16]=[CH:15][C:11]=3[C:12](=[O:14])[CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

Conditions

Temperature: 10 °C

Procedure

2-(1-Bromocyclohexyl)-8-bromomethyl-4-oxo-4H-[1]-benzopyran (11.2 g, 0.028 mole) was dissolved in dimethylformamide (200 ml) and to the solution was added NaCN (1.5 g, 0.0305 mole) with stirring at 10° C. The mixture was stirred for 30 minutes. Water was added to the reaction mixture and crystals precipitated were filtered off. The crude crystals were purified by silica gel chromatography (eluent: chloroform-hexane (10:1)) to obtain the title compound (4.08 g), yield 44.7 %. The product was recrystallized from ethyl acetate to obtain prisms, m.p. 144°-145° C.

Workup

stirringThe mixture was stirred for 30 minutes
customprecipitated
filtrationwere filtered off
customThe crude crystals were purified by silica gel chromatography (eluent: chloroform-hexane (10:1))

Sources & evidence

ORD record: ord-a100227d24974c2bbf0d548452a9c017
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04904690

Reaction notes

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