Iodoethane → 2-Ethyl-4-(5-methyl-2-furyl)-butane nitrile

HRID 647023Notes

Reaction equation

[CH2:1]([N-]CC)[CH3:2].[Li+].[Li].C(NCC)C.[CH3:13][C:14]1[O:18][C:17]([CH2:19][CH2:20][CH2:21][C:22]#[N:23])=[CH:16][CH:15]=1.C(I)C>C1C=CC=CC=1.CN(C)P(=O)(N(C)C)N(C)C.O.CCOCC.O1CCCC1>[CH2:1]([CH:21]([CH2:20][CH2:19][C:17]1[O:18][C:14]([CH3:13])=[CH:15][CH:16]=1)[C:22]#[N:23])[CH3:2]

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of lithium diethyl amide prepared from 0.7 g (0.1 mol) lithium and 7.3 g (0.1 mol) diethyl amine in 44 ml benzene/hexamethyl phosphoric acid triamide 1:1 (2 hours at 25° C.) was added dropwise under nitrogen to a mixture which had been cooled down to -70° C. of 14.9 g (0.1 mol) 4-(5-methyl-2-furyl)-butane nitrile, 15.6 g (0.1 mol) ethyl iodide, 20 ml dry tetrahydrofurane and 140 ml dry ether. The mixture obtained was stirred for one hour at -70° C., was slowly heated up to 10° C. and then poured into cold water. The organic layer was separated off, washed with water and dried on anhydrous magnesium sulphate. The solvent was evaporated off under reduced pressure and the residue was subjected to chromatography over 300 g silicagel with hexane/ethyl acetate 95:5. Initially 2.3 g dl-2,2-diethyl-4-(5-methyl-2-furyl)-butane nitrile was eluated, followed by 9.5 g (58% yield) dl-2-ethyl-4-(5-methyl-2-furyl)-butane nitrile.

Workup

additionwas added dropwise under nitrogen to a mixture which
customThe mixture obtained
temperaturewas slowly heated up to 10° C.
customThe organic layer was separated off
washwashed with water
dry with materialdried on anhydrous magnesium sulphate
customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record: ord-a2b967c202864099a1b098a19fb3260e
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04407753

Reaction notes

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