Sodium Cyanide → Isopropyl 4-cyano-5-ethylthiophene-2-carboxylate

HRID 2298637노트

반응식

HRID 2298637 반응식
Br[C:2]1[CH:3]=[C:4]([C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[S:5][C:6]=1[CH2:7][CH3:8].[Cu](C#N)[C:16]#[N:17].[C-]#N.[Na+]>CN(C)C=O>[CH2:7]([C:6]1[S:5][C:4]([C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])=[CH:3][C:2]=1[C:16]#[N:17])[CH3:8]

참가 물질

5

반응물 3

HCID 8929Sodium CyanideHCID 18536986Isopropyl 4-bromo-5-ethylthiophene-2-carboxylateHCID 178418260HCID 178418260, 화합물

생성물 1

HCID 18537065Isopropyl 4-cyano-5-ethylthiophene-2-carboxylate수율 53%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A stirred solution of 4 g (14.4 mmol) of isopropyl 4-bromo-5-ethylthiophene-2-carboxylate was refluxed in dry dimethylformamide (50 mL) with copper cyanide (1.94 g, 22 mmol) for 8 hours. The cooled mixture was poured into 0.1 M sodium cyanide (500 mL) and extracted with diethyl ether (4×50 mL). The organic layers were washed twice with brine (50 mL) and dried over anhydrous sodium sulfate. The solvents were removed in vacuo. Column chromatography on silica gel (400 g), eluting with hexanes:ethyl acetate 9/1 (v:v) gave isopropyl 2-ethyl-3-cyano-thiophene-5-carboxylate (1.7 g, 53%) as a pale yellow oil. 1H-NMR (DMSO-d6; 300 MHz) δ8.03 (s, 1H), 5.10 (septet, 1H, J=6.2 Hz), 3.04 (q, 2H, J=7.5 Hz), 1.31 (t, 3H, J=7.5 Hz), 1.30 (d, 6H, J=6.2 Hz). Mass spectrum (ESI m/z): Calcd. for C11H13NO2S 224.1 (M+H), found 224.0.

후처리

  1. extractionextracted with diethyl ether (4×50 mL)
  2. washThe organic layers were washed twice with brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvents were removed in vacuo
  5. washColumn chromatography on silica gel (400 g), eluting with hexanes

출처 및 근거

ORD 기록
ord-5893591dae844259955b8563adcc4d92
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06492403B1

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