Triethylamine → HCID 13449587, compound

HRID 1918652Notes

Reaction equation

HRID 1918652 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)#[CH:2].Cl[C:10](=[N:16][OH:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(N(CC)CC)C>ClC(Cl)C.C[C]1[C](C)[C](C)[C](C)[C]1C.C1CC=CCCC=C1.Cl[Ru]>[C:3]1([C:1]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:16][O:17][CH:2]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 6816376Ethyl chloro(hydroximino)acetate

Product 1

HCID 13449587HCID 13449587, compoundYield 5.1%

Reagents, catalysts & solvents 2

HCID 178420236HCID 178420236, compoundCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

Ethynylbenzene (0.300 mL; 2.73 mmol) and ethyl 2-chloro-2-(hydroxyimino)acetate (0.455 g; 3.00 mmol) were dissolved in degassed dichloroethane (15 mL), chloro(1,5-cyclooctadiene)(pentamethylcyclopentadienyl)ruthenium (II) (0.052 g; 0.136 mmol) and triethyl amine (0.476 mL; 3.41 mmol) were added and the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was then filtered through a pad of silica gel and the filtrate was concentrated under reduced pressure. The crude material was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in heptane) and by preparative HPLC method 3 to yield 0.030 g (5%) of the title compound as a solid.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of silica gel
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude material was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in heptane) and by preparative HPLC method 3

Sources & evidence

ORD record
ord-fcc20c8501f441d1b89c63f40731f743
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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