Potassium sodium tartarate → HCID 178442087, compound

HRID 370700Notes

Reaction equation

[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:5][CH2:4]1)#N.[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=[O:39].[Na+].[K+]>C(Cl)Cl.C1(C)C=CC=CC=1>[CH2:23]([C:20]1[CH:19]=[CH:18][C:17]([C:14]2[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][C@H:6]3[CH2:7][CH2:8][C@H:3]([CH:1]=[O:39])[CH2:4][CH2:5]3)=[CH:16][CH:15]=2)=[CH:22][CH:21]=1)[CH2:24][CH2:25][CH2:26][CH3:27]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 2.6 g of 4-[2-(trans-4-cyanocyclohexyl)ethyl]-4'-pentylbiphenyl in 100 ml of methylene chloride was placed at -78° C. in a sulphonation flask under argon gasification and treated within 5 minutes with 9.5 ml of a 1.5N soution of diisobutylaluminium hydride in toluene. The mixture was subsequently stirred at -78° C. for a further 4.5 hours, then poured into 100 ml of 10% potassium sodium tartrate solution and extracted three times with 100 ml of methylene chloride each time. The organic phases were washed once with 100 ml of 10% potassium sodium tartrate solution, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (2.93 g) on silica gel with ethyl acetate as the eluant gave 2.33 g (89%) of trans-4-[2-(4'-pentyl-4-biphenylyl)ethyl]cyclohexanecarboxaldehyde as colourless crystals.

Workup

extractionextracted three times with 100 ml of methylene chloride each time
washThe organic phases were washed once with 100 ml of 10% potassium sodium tartrate solution
dry with materialdried over magnesium sulphate
concentrationconcentrated

Sources & evidence

ORD record: ord-ae8a31d21ae24de1a71a49be89f26644
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04528114

Reaction notes

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