Methanol → HCID 14986697, compound

HRID 1494139Notes

Reaction equation

HRID 1494139 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:13]=1)[C:7](OCC)=[O:8].[H-].C([Al+]CC(C)C)C(C)C.CO.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl.[Cl-].[Na+].O.CCOCC>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:13]=1)[CH:7]=[O:8]

Participants

8

Reactant 4

HCID 887MethanolHCID 24436Sodium SulfateHCID 14986696HCID 14986696, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14986697HCID 14986697, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 0.54 g (1.6 mmol) ethyl 6-chloro-2[m-(3-pyridyl)phenyl]hexanoate in 10 mL methylene chloride at -78° C. is added slowly 2.2 mL (3.4 mmol) of a 1.5 M solution of diisobutylaluminum hydride in hexanes. The reaction is stirred at -78° C. for 5 minutes and 1.6 mL methanol is added followed by 50 mL ether. The mixture is warmed to 0° C. and 1.6 mL brine and 1.11 g finely powdered sodium sulfate are added. The mixture is stirred and then filtered. The filter cake is washed with methylene chloride and combined organic layer is evaporated to give 6-chloro-2-[m-(3-pyridyl)phenyl]hexanal as an oil; IR (CH2Cl2): 1724, 1682 cm-1.

Workup

  1. temperatureThe mixture is warmed to 0° C.
  2. stirringThe mixture is stirred
  3. filtrationfiltered
  4. washThe filter cake is washed with methylene chloride and combined organic layer
  5. customis evaporated

Sources & evidence

ORD record
ord-65e4d6ccb4494e84b489066e321b13eb
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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