HCID 53933867, compound → HCID 10757911, compound

HRID 1586213Notes

Reaction equation

HRID 1586213 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=2)=[CH:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]>C(OCC)(=O)C.C1COCC1>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][CH2:15][CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:18][CH:19]=1)#[N:24]

Participants

3

Reactant 1

HCID 53933867HCID 53933867, compound

Product 1

HCID 10757911HCID 10757911, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

Part C. The methyl 3-(3-cyanophenyl)-5-(4-cyanophenyl)-2,4-pentadienoate (5) (0.328 gm, 1.04 mmol) was dissolved in ethyl acetate/THF (1:1) and was degassed with N2. A catalytic amount of 10% Pd on carbon was added and the flask was placed on a Parr shaker for 1 hour at 45 p.s.i. The contents of the flask are filtered through Celite and the filtrate was concentrated under vacuum. The residue was chromatographed on silica gel eluting ethyl acetate:hexanes (25:75, v:v) to give methyl 4-(cyano)-beta-[3-(cyano)phenyl]benzene pentanoate as an oil 0.190 gm (57%). MS: (M+NH4)+ 336; 1H NMR (CDCl3): 1.95 (m, 1H), 2.05 (m, 1H), 2.55 (m, 2H), 2.65 (ddd, 2H), 3.15 (m, 1H), 3.60 (s, 3H), 7.20 (d, 2H), 7.45 (d, 2H), 7.50 (s, 1H), 7.55 (m, 3H).

Workup

  1. customwas degassed with N2
  2. additionA catalytic amount of 10% Pd on carbon was added
  3. filtrationThe contents of the flask are filtered through Celite
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe residue was chromatographed on silica gel
  6. washeluting ethyl acetate:hexanes (25:75, v:v)

Sources & evidence

ORD record
ord-d021869fe60d412b9820ee5aaaadc26e
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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