Water → HCID 68487863, compound

HRID 1874979Notes

Reaction equation

HRID 1874979 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].Cl[Sn]Cl.O.[CH3:15][CH2:16][O:17]C(C)=O>ClCCCl>[C:16]([C:5]1[NH:4][C:3]([C:7]([O:9][CH3:10])=[O:8])=[C:2]([Cl:1])[CH:6]=1)(=[O:17])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24479Stannous ChlorideHCID 5324605Methyl 3-chloro-1H-pyrrole-2-carboxylate2×

Product 1

HCID 68487863HCID 68487863, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of methyl 3-chloro-1H-pyrrole-2-carboxylate (0.100 g, 0.627 mmol) in DCE (3 mL) was added to a suspension of SnCl2 (0.238 g, 1.25 mmol) and methyl 3-chloro-1H-pyrrole-2-carboxylate (0.100 g, 0.627 mmol) in DCE (3 mL) at 0° C. The reaction was stirred for 10 min. at 0° C. then warmed to room temp over 2 hours. The reaction mixture was poured into water and EtOAc and the organic layer was separated, then washed with 1N sodium hydroxide, dried over MgSO4, filtered and evaporated to a residue. Purification was accomplished on silica with EtOAc and hexanes to afford the title compound (0.034 g, 26%) as a solid, along with methyl 4-acetyl-3-chloro-1H-pyrrole-2-carboxylate (0.047 g, 37%) as a solid. 1H NMR (400 MHz, CDCl3) δ ppm 9.90 (br. s., 1H), 6.79 (s, 1H), 3.89 (s, 3H), 2.43 (s, 3H). LCMS: m/z 200.0 (M−1).

Workup

  1. temperaturethen warmed to room temp over 2 hours
  2. customthe organic layer was separated
  3. washwashed with 1N sodium hydroxide
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to a residue
  7. customPurification

Sources & evidence

ORD record
ord-e1d79203782148f08be3f31517cfe064
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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