Reacción #564477

ord-38f0abb22a7c490781e934cf79a4cd41

Ecuación de reacción

CC(C)NC(C)C
diisopropylamine
CCCC#N
butyronitrile
CCCCCCCCc1ccc(-c2ccc([C@H]3CC[C@H](CI)CC3)cc2)cc1
trans-4-(4'-octylbiphenyl-4-yl)cyclohexylmethyl iodide
CCCCCCCCc1ccc(-c2ccc([C@H]3CC[C@H](C(=O)O)CC3)cc2)cc1
trans-4-(4'octylbiphenyl-4-yl)cyclohexanecarboxylic acid
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
CS(=O)(=O)[O-]
mesylate
[I-].[Na+]
NaI
→
CCCCCCCCc1ccc(-c2ccc([C@H]3CC[C@H](CC(C#N)CC)CC3)cc2)cc1
4-octyl-4'-[trans-4-(2-cyanobutyl)cyclohexyl]biphenyl

Reactantes

—
nitrile
—
alcohol
CC(C)NC(C)C
diisopropylamine
CCCC#N
butyronitrile
CCCCCCCCc1ccc(-c2ccc([C@H]3CC[C@H](CI)CC3)cc2)cc1
trans-4-(4'-octylbiphenyl-4-yl)cyclohexylmethyl iodide
CCCCCCCCc1ccc(-c2ccc([C@H]3CC[C@H](C(=O)O)CC3)cc2)cc1
trans-4-(4'octylbiphenyl-4-yl)cyclohexanecarboxylic acid
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
CS(=O)(=O)[O-]
mesylate
[I-].[Na+]
NaI

Reactivos

Ninguno

Disolventes

C1CCOC1
tetrahydrofuran
CC(C)=O
acetone

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.WAITis carried out for a further hour

Procedimiento

With air and moisture excluded, 9.4 ml of diisopropylamine, 4.6 g of butyronitrile and 30 g of trans-4-(4'-octylbiphenyl-4-yl)cyclohexylmethyl iodide [obtainable from trans-4-(4'octylbiphenyl-4-yl)cyclohexanecarboxylic acid (which can in turn be prepared by saponification of the nitrile) by reduction with LiAlH4, conversion of the alcohol into the corresponding mesylate and subsequent Finkelstein reaction with NaI in acetone] are added in sequence to 50 ml of tetrahydrofuran at -50°. After heating to room temperature, stirring is carried out for a further hour and 4-octyl-4'-[trans-4-(2-cyanobutyl)cyclohexyl]biphenyl is obtained after the usual working up.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04886620uspto-grants-1989_12