Tetrahydrofuran → Ethyl 3-(acetylthio)-3-cyanopropanoate

HRID 882673

반응식

HRID 882673 반응식
[C:1](/[CH:3]=[CH:4]\[C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:2].[S:10]1C=CC=C1CC(O)=O.CCN(C(C)C)C(C)C.C1C[O:31][CH2:30][CH2:29]1>>[C:30]([S:10][CH:3]([C:1]#[N:2])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:31])[CH3:29]

참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran2회HCID 159702-Thiopheneacetic acidHCID 81531DiisopropylethylamineHCID 15577688Ethyl (2Z)-3-cyanoprop-2-enoate

생성물 1

HCID 53248108Ethyl 3-(acetylthio)-3-cyanopropanoate수율 65%

실험 절차

(Z)-ethyl 3-cyanoacrylate (5.01 g, 40.00 mmol) in 80 ml of THF at −20° C. was added the solution of thiol acetic acid (5.0 ml, 70.15 mmol) and DIPEA (16.0 ml, 92.03 mmol) in 20 ml of THF in 30 min. The reaction was kept at −20° C. for 4 hr then room temperature overnight. The mixture was concentrated, diluted with CH2Cl2, washed with saturated NaHCO3, dried over MgSO4, filtered, evaporated and purified by SiO2 chromatography (1:4 EtAC/Hexane) to afford 5.22 g (65%) of the title compound. Rf=0.25 (1:4 EtAC/Hexane); 1H NMR (CDCl3), 4.44 (m, 1H), 4.11 (dd, 2H, J=7.1, 14.3 Hz), 3.38 (m, 1H), 3.15 (m, 1H), 2.17 (s, 3H), 1.19 (t, 3H, J=7.2 Hz); 13C NMR 194.12, 173.21, 119.82, 61.35, 33.52, 30.08, 14.62; MS m/z+ 225.9 (MW+Na), m/z− 201.7 (MW−H).

후처리

  1. customroom temperature overnight
  2. concentrationThe mixture was concentrated
  3. additiondiluted with CH2Cl2
  4. washwashed with saturated NaHCO3
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. custompurified by SiO2 chromatography (1:4 EtAC/Hexane)

출처 및 근거

ORD 기록
ord-ba6cdf2b3bb44480aa7b805b882d90d0
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236319B2

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