Isobutyronitrile → 2,9-Dicyano-2,9-dimethyldecane

HRID 258463

Reaction equation

HRID 258463 reaction equation
[C:1]([C:3]([CH3:23])([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]CCCCCCCCCC)[CH3:4])#[N:2].C([Li])CCC.[CH:29]([NH:32]C(C)C)(C)C.[C:36](#N)C(C)C.BrCCCCCCBr>O1CCCC1>[C:29]([C:11]([CH3:12])([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:3]([C:1]#[N:2])([CH3:4])[CH3:23])[CH3:36])#[N:32]

Participants

7

Reactant 5

HCID 6559IsobutyronitrileHCID 7912DiisopropylamineHCID 123681,6-DibromohexaneHCID 197812072-Cyano-2-methyleicosaneHCID 178418339Butyllithium

Product 1

HCID 197812052,9-Dicyano-2,9-dimethyldecane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By the procedure used to prepare the compound of Example 2, the title compound is prepared from 24 mL of a 2.5M n-butyllithium solution in hexanes, 6.07 g of diisopropylamine, 5.5 mL of isobutyronitrile, 7.32 g of 1,6-dibromohexane, and 120 mL of tetrahydrofuran. The IR and 1H NMR spectra of the white solid (7.7 g) obtained were consistent with structure of the desired product.

Sources & evidence

ORD record
ord-0ebf857b948a47fc993f27b4d2982bd9
Source dataset
uspto-grants-1993_11
Patent number
US05266726

Linked notes

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