Water → 2,6-Dichloro-4-morpholin-4-YL-benzaldehyde

HRID 1513234

반응식

HRID 1513234 반응식
[Li]C(CC)C.[Cl:6][C:7]1[CH:8]=[C:9]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:10]=[C:11]([Cl:13])[CH:12]=1.CN([CH:23]=[O:24])C.O>C1COCC1>[Cl:6][C:7]1[CH:8]=[C:9]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:10]=[C:11]([Cl:13])[C:12]=1[CH:23]=[O:24]

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 669665754-(3,5-Dichlorophenyl)morpholineHCID 178418400CID 53628100

생성물 1

HCID 71486052,6-Dichloro-4-morpholin-4-YL-benzaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Add sec-BuLi (1.4M in cyclohexane, 5.44 mL) in a dropwise manner to a solution of 4-(3,5-Dichloro-phenyl)-morpholine (Tetrahedron (2001), 57(36), 7657-7664, 1.60 g, 6.93 mmol) in dry THF (20 mL) under N2 at −78° C. Allow to stir for 30 min. Slowly add DMF (2.68 mL, 34.7 mmol) to the cold solution. Upon disappearance of the starting material by TLC, warm the reaction to 0° C. Quench the reaction by addition of H2O (15 mL) and extract the mixture with EtOAc (150 mL). Dry the organic phase over Na2SO4 and evaporate the solvent. Triturate the resulting solid with Et2O to yield the title compound. Evaporate the filtrate to yield another crop of the title compound as a yellow solid: 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm 3.46-3.54 (m, 4 H) 3.85-3.93 (m, 4 H) 7.06 (s, 2 H) 10.44(s, 1 H); MS (m/z) 260.0 (M+1).

후처리

  1. temperatureUpon disappearance of the starting material by TLC, warm
  2. customthe reaction to 0° C
  3. customQuench
  4. customthe reaction
  5. extractionextract the mixture with EtOAc (150 mL)
  6. dry with materialDry the organic phase over Na2SO4
  7. customevaporate the solvent
  8. customTriturate the resulting solid with Et2O

출처 및 근거

ORD 기록
ord-76c72d6dd2264d509af1f95cf430f3fb
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217065B2

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