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

HRID 647023노트

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HRID 647023 반응식
[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]

참가 물질

10

반응물 5

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

생성물 1

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

시약·촉매·용매 4

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 86739045Benzene hexamethyl phosphoric acid triamide용매

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온도
-70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a2b967c202864099a1b098a19fb3260e
출처 데이터셋
uspto-grants-1983_10
특허 번호
US04407753

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