HCID 54223121, compound → HCID 18614943, compound

HRID 1265258Notes

Reaction equation

HRID 1265258 reaction equation
[C:1]([C:5]1[C:6]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:7]([C:15]([CH3:19])=[CH:16][C:17]#[N:18])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([C:5]1[C:6]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:7]([CH:15]([CH3:19])[CH2:16][C:17]#[N:18])[CH:8]=[C:9]([C:11]([CH3:12])([CH3:13])[CH3:14])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 54223121HCID 54223121, compound

Product 1

HCID 18614943HCID 18614943, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(3,5-di-t-butyl-2-n-heptyloxyphenyl)-but-2-enenitrile (900 mg, 2.64 mmol) in EtOAc (5 mL) was added 10% Pd on carbon (20 mg, catalytic amount). The mixture was placed under vacuum for 1 min followed by addition of H2. After stirring for 24 h under an atmosphere of H2, the solution was filtered through celite. The celite washed with EtOAc (3×5 mL) and the solution was concentrated to give the reduced product 3-(3,5-di-t-butyl-2-n-heptyloxyphenyl)-butyronitrile 880 mg (97%): TLC (5% EtOAc-95% hexanes) Rf0.8; 1H-NMR (CDCl3) δ 7.00(d, J=2.2 Hz, 1H, Ar—H) 6.89(d, J=2.2 Hz, 1H Ar—H), 3.73 (t, J=6.5 Hz, 2H, OCH2), 3.52(m, 1H, CH), 3.27(m, 1H, CH), 2.86(m, 1H, CH), 2.63(m, 2H, CH2CN), 1.79(m, 2H, CH2), 1.50(m, 2H, CH2), 1.44(m, 6H, 3CH2), 1.39(d, J=13.2 Hz, 3H, CH3), 1.27(d, J=4.7 Hz, 2CH3), 1.21(d, J=4.7 Hz, 2CH3), 0.89(t, J=6.6 Hz, 3H, CH3).

Workup

  1. additionfollowed by addition of H2
  2. filtrationthe solution was filtered through celite
  3. washThe celite washed with EtOAc (3×5 mL)
  4. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-a7f7cb0a518e43b2a1782e48d6ddca16
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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