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

HRID 647023ノート

反応式

HRID 647023 の反応式
[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]

参加物

10

反応物 5

HCID 6340IodoethaneHCID 8021DiethylamineHCID 3028194LithiumHCID 11137085Lithium diethylamideHCID 204854764-(5-Methyl-2-furyl)-butane nitrile

生成物 1

HCID 204854592-Ethyl-4-(5-methyl-2-furyl)-butane nitrile収率 58%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 86739045Benzene hexamethyl phosphoric acid triamide溶媒

反応条件

温度
-70 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-a2b967c202864099a1b098a19fb3260e
出典データセット
uspto-grants-1983_10
特許番号
US04407753

反応ノート

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