Monocrotaline → Monocrotaline pyrrole

HRID 2173747Notes

Reaction equation

HRID 2173747 reaction equation
[CH3:1][C@@H:2]1[C@:19]([OH:21])([CH3:20])[C@:18]([OH:23])([CH3:22])[C:16](=[O:17])[O:15][CH2:14][C:11]2=[CH:12][CH2:13][N:9]3[C@H:10]2[C@@H:6]([CH2:7][CH2:8]3)[O:5][C:3]1=[O:4].C1(Cl)C(Cl)=C(Cl)C(=O)C(=O)C=1Cl>C(Cl)(Cl)Cl>[CH3:1][C@@H:2]1[C@:19]([OH:21])([CH3:20])[C@:18]([OH:23])([CH3:22])[C:16](=[O:17])[O:15][CH2:14][C:11]2[CH:12]=[CH:13][N:9]3[C:10]=2[C@@H:6]([CH2:7][CH2:8]3)[O:5][C:3]1=[O:4]

Participants

4

Reactant 2

HCID 9415MonocrotalineHCID 73252o-Chloranil

Product 1

HCID 104764Monocrotaline pyrrole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To monocrotaline (20 mg) dissolved in chloroform (5 mL) was added a solution of o-chloranil (25 mg) in chloroform (5 mL). After 5 min, TLC (Thin layer Chromatography) showed that most of starting material was consumed and the mixture was shaken vigorously with a cooled (0-5° C.) solution, which contained 700 mg KOH and 20 mg NaBH4 in 1 mL water for 10-15 sec. The organic phase was separated, immediately dried with anhydrous Na2SO4 and concentrated under reduced pressure to give dehydromonocrotaline (DHM). The chemical reaction was depicted in FIG. 21.

Workup

  1. customwas consumed
  2. customfor 10-15 sec
  3. customThe organic phase was separated
  4. dry with materialimmediately dried with anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6aa4d44ebbe64719b448cc4ee2727974
Source dataset
uspto-grants-2015_06
Patent number
US09056916B2

Reaction notes

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