Potassium sodium tartarate → HCID 178444462, compound

HRID 370691Notes

Reaction equation

HRID 370691 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]#N)[CH2:16][CH2:15]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=[O:33].[Na+].[K+]>C(Cl)Cl.C1(C)C=CC=CC=1>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([CH:20]=[O:33])[CH2:16][CH2:15]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 178444461HCID 178444461, compound

Product 1

HCID 178444462HCID 178444462, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 2.3 g of trans-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexanecarbonitrile in 100 ml of methylene chloride was placed at -78° C. in a sulphonation flask under argon gasification and treated within 3 minutes with 10.5 ml of a 1.5M solution of diisobutylaluminium hydride in toluene. The mixture was subsequently stirred at -78° C. for a further 4 hours, then treated cautiously with 50 ml of 10% potassium sodium tartrate solution and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed twice with 50 ml of water each time and once with 50 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (2.1 g) on silica gel with 5% ethyl acetate/petroleum ether gave 1.95 g (84.4%) of trans-4-[2-(trans-4-pentylcyclohexyl)ethyl]cyclohexanecarboxaldehyde which contained about 10% of the corresponding epimeric cis aldehyde in accordance with NMR spectroscopic analysis and which was reacted without additional purification.

Workup

  1. extractionextracted three times with 100 ml of diethyl ether each time
  2. washThe organic phases were washed twice with 50 ml of water each time
  3. dry with materialonce with 50 ml of saturated sodium chloride solution, dried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d44e3a2c209b45bfbbaba16697205a3e
Source dataset
uspto-grants-1985_07
Patent number
US04528114

Reaction notes

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