Tri-o-tolylphosphine → HCID 69663864, compound

HRID 324577Notes

Reaction equation

HRID 324577 reaction equation
[CH3:1][C:2]([CH3:20])([CH2:18][CH3:19])[C:3](=[O:17])[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11](=[O:16])[CH2:12][CH2:13][CH:14]=[CH2:15])=[O:5].[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32](Br)=[CH:31][CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][C:2]([CH3:20])([CH2:18][CH3:19])[C:3](=[O:17])[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11](=[O:16])[CH2:12][CH2:13][CH:14]=[CH:15][C:32]1[CH:33]=[CH:34][C:29]([O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:30][CH:31]=1)=[O:5]

Participants

6

Reactant 3

HCID 80271Tri-o-tolylphosphineHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 22257788HCID 22257788, compound

Product 1

HCID 69663864HCID 69663864, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 3,3-dimethyl-1-(2-pent-4-enoylpyrrolidinyl)pentane-1,2-dione (1.73 g; 6.20 mmol), 4-benzyloxybromobenzene (1.80 g; 6.83 mmol), palladium (II) acetate (70 mg; 0.31 mmol), and tri(orthotolyl)phosphine (380 mg; 1.24 mmol) in triethylamine (23 ml) was refluxed overnight. The mixture was concentrated in vacuo and purified on a silica gel column, eluting with a gradient from 10% ethyl acetate/hexane to 20% ethyl acetate/hexane, to obtain 1.72 g (60%) of 3,3-dimethyl-1-(2-{5-[4-(phenylmethoxy)phenyl]pent-4-enoyl}pyrrolidinyl)pentane-1,2-dione as a yellow oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified on a silica gel column
  3. washeluting with a gradient from 10% ethyl acetate/hexane to 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-4ce72148170c471da0fadc0f68790a20
Source dataset
uspto-grants-2001_04
Patent number
US06218424B1

Reaction notes

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