HCID 54028697, compound → HCID 53712757, compound

HRID 1490041Notes

Reaction equation

HRID 1490041 reaction equation
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[CH:24][C:25]([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[O:26])=[CH:19][CH:18]=2)=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[C:1]1([C:7]([C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[O:26])=[CH:21][CH:22]=2)=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH3:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 54028697HCID 54028697, compound

Product 1

HCID 53712757HCID 53712757, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 1140TolueneSolvent

Procedure

A solution of 50 mg (0.12 mmol) of 3-[4-(1,2-Diphenyl-but-1-enyl)-phenyl]-N,N-diethyl acrylamide (see Example 2) and 3 mg of tris(triphenylphosphine)-rhodium(I) chloride (Wilkinson's catalyst) in 1 mL dry toluene was stirred over an atmosphere of H2 gas at 50° C. for 16 h. The solution was cooled to RT and the toluene removed in vacuo. Purification of the residue by silica gel flash chromatography using hexane/ethyl acetate 2/1 as eluent afforded 48 mg (95%) of the desired compound named above of the desired compound named above as a clear, colorless oil: 1H NMR (CDCl3, 300 MHz) s 7.37-7.11 (m, 10 H), 6.85 (d, 2 H, J=8.3), 6.78 (d, 2 H, J=8.3) 3.31 (q, 2 H, J=7.1), 3.08 (q, 2 H, J=7.3), 2.81 (t, 2 H, J=8.3), 2.44 (m, 4 H) 1.03(m,6 H), 0.91 (t, 3 H, J=7.3); low resolution MS m/e 412 (MH+); Anal. (C29H33NO) C, H, N. [see, for example (i), Scheme C, supra].

Workup

  1. customthe toluene removed in vacuo
  2. customPurification of the residue by silica gel flash chromatography

Sources & evidence

ORD record
ord-429ab8bc3c394d9587217379bed533db
Source dataset
uspto-grants-1997_10
Patent number
US05681835

Reaction notes

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