Triethylamine → HCID 178459282, compound

HRID 366973Notes

Reaction equation

HRID 366973 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH3:6][Mn:7](C(O)C)([CH:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1)(=[C:12]=[O:13])(=[C:10]=[O:11])=[C:8]=[O:9].[CH2:22](N(CC)CC)[CH3:23]>ClCCl>[CH3:6][Mn:7]([CH:2]([C:1](=[O:4])[CH:22]=[CH2:23])[CH3:3])([CH:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1)(=[C:10]=[O:11])(=[C:12]=[O:13])=[C:8]=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 178462376HCID 178462376, compound

Product 1

HCID 178459282HCID 178459282, compoundYield 108.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acryloyl chloride (9 grams), methyl(α-hydroxyethyl)-cyclopentadienyltricarbonylmanganese (13.1 grams), and triethylamine (10.1 grams) were dissolved in 200 ml dichloromethane under a nitrogen atmosphere. A 0.1 gram sample of N,N-dimethylaminopyridine (DMAP) was added as a catalyst. For 4 days the solution was stirred and protected from light while and a white precipitate slowly formed. The reaction mixture was extracted twice with dilute HCl and the dichloromethane phase was dried with magnesium sulfate. The magnesium sulfate was removed by filtration and the dichloromethane solution was filtered through silica gel to remove a colored impurity. The solution was then rotary evaporated to a yellowish oil that was vacuum dried to give 16.2g (97%) of methyl(α-acryloylethyl)cyclopentadienyl-tricarbonylmanganese as a mixture of 1,2 and 1,3 isomers.

Workup

  1. customa white precipitate slowly formed
  2. extractionThe reaction mixture was extracted twice with dilute HCl
  3. dry with materialthe dichloromethane phase was dried with magnesium sulfate
  4. customThe magnesium sulfate was removed by filtration
  5. filtrationthe dichloromethane solution was filtered through silica gel
  6. customto remove a colored impurity
  7. customThe solution was then rotary evaporated to a yellowish oil that
  8. customdried

Sources & evidence

ORD record
ord-515c15931a464e84bcadbac6b83b6f14
Source dataset
uspto-grants-2000_10
Patent number
US06132860

Reaction notes

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