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

HRID 1360737

Reaction equation

HRID 1360737 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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, 4H) 3.85-3.93 (m, 4H) 7.06 (s, 2H) 10.44 (s, 1H); MS (m/z) 260.0 (M+1).

Workup

  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

Sources & evidence

ORD record
ord-86788a996c8a47ec8d8d98497eef0140
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Linked notes

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