Methanol → HCID 14986697, compound

HRID 465600Notes

Reaction equation

HRID 465600 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.CCCCCC.[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

9

Reactant 4

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

Product 1

HCID 14986697HCID 14986697, compound

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 57417360Sodium chloride; waterSolvent

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° is added slowly 2.2 ml (3.4 mmol) of a 1.5M solution of diisobutylaluminium hydride in hexane. The reaction mixture is stirred at -78° for 5 min and 1.6 ml methanol is added followed by 50 ml ether. The mixture is warmed to 0° 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°
  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-f08dfdb045da4ffcb46dd199a6e41f1f
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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