Aluminium lithium hydride → 1-(Trifluoromethyl)cyclopropanecarboxaldehyde

HRID 1526635노트

반응식

HRID 1526635 반응식
CON(C)[C:4]([C:6]1([C:9]([F:12])([F:11])[F:10])[CH2:8][CH2:7]1)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C.C1COCC1>[F:10][C:9]([F:12])([F:11])[C:6]1([CH:4]=[O:5])[CH2:8][CH2:7]1

참가 물질

5

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 57785368N-methoxy-N-methyl-1-(trifluoromethyl)cyclopropane-1-carboxamide

생성물 1

HCID 574451861-(Trifluoromethyl)cyclopropanecarboxaldehyde수율 38.6%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a solution of N-methoxy-N-methyl-1-(trifluoromethyl)cyclopropanecarboxamide (0.23 g, 1.162 mmol) in diethyl ether (3 mL, aldrich) at 0° C. under Ar(g) was added lithium aluminium hydride (1.0 M solution in THF; 1.39 mL, 1.39 mmol, aldrich) dropwise. After completed addition the reaction was then stirred at 0° C. for 45 min. The reaction was quenched with a solution of KHSO4 (1M) at −78° C. and gradually warmed to RT and stirred for 30 min. The reaction was extracted with diethyl ether (2×10 mL). The combined organic extracts were dried over MgSO4, concentrated, and dried in vacuo to afford 62 mg of the title compound as a light yellow liquid, which was used in the next step without further purification. 1H NMR (CHLOROFORM-d) δ: 9.69 (s, 1H), 1.43 (m, 2H), 1.21 (t, J=7.0 Hz, 2H)

후처리

  1. additionaddition the reaction
  2. customThe reaction was quenched with a solution of KHSO4 (1M) at −78° C.
  3. temperaturegradually warmed to RT
  4. stirringstirred for 30 min
  5. extractionThe reaction was extracted with diethyl ether (2×10 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. concentrationconcentrated
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-9d04e021b71f42f99ee0047ba1ecc4fb
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085576B2

반응 노트

불러오는 중…