Sodium Iodide → HCID 178442631, compound

HRID 1461498Notes

Reaction equation

HRID 1461498 reaction equation
C(NC(C)C)(C)C.[C:8](#[N:12])[CH2:9][CH2:10][CH3:11].[CH2:13]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C@H:33]3[CH2:38][CH2:37][C@H:36]([CH2:39]I)[CH2:35][CH2:34]3)=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(C1C=CC(C2C=CC([C@H]3CC[C@H](C(O)=O)CC3)=CC=2)=CC=1)CCCCCCC.[H-].[H-].[H-].[H-].[Li+].[Al+3].S([O-])(=O)(=O)C.[Na+].[I-]>CC(C)=O.O1CCCC1>[CH2:13]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C@H:33]3[CH2:38][CH2:37][C@H:36]([CH2:39][CH:9]([C:8]#[N:12])[CH2:10][CH3:11])[CH2:35][CH2:34]3)=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

10

Reactant 7

HCID 5238Sodium IodideHCID 7912DiisopropylamineHCID 8008ButyronitrileHCID 85257MethanesulfonateHCID 21226445Aluminium lithium hydrideHCID 178442632HCID 178442632, compoundHCID 178442633HCID 178442633, compound

Product 1

HCID 178442631HCID 178442631, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. waitis carried out for a further hour

Sources & evidence

ORD record
ord-8386e2988f534eac958c8a70422a4181
Source dataset
uspto-grants-1991_12
Patent number
US05075032

Reaction notes

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