Pyrrolidine → HCID 54319926, compound

HRID 1684619Notes

Reaction equation

HRID 1684619 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([CH:12]=O)[CH:5]=1.[CH2:15]([O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[O:29][CH2:28][CH2:27][C:26]2=[O:33])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1CCCC1>CO>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([CH:12]=[C:27]2[C:26](=[O:33])[C:25]3[C:30](=[CH:31][CH:32]=[C:23]([O:22][CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:24]=3)[O:29][CH2:28]2)[CH:5]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 144227766-(Benzyloxy)chroman-4-oneHCID 15192109Methyl 3-formyl-4-methoxybenzoate

Product 1

HCID 54319926HCID 54319926, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

19.1 g (98.3 mmol) of 3-formyl-4-methoxybenzoic acid methyl ester (from Example 37) were added to a room temperature suspension of 25.0 g (98.3 mmol) of 6-benzyloxychroman-4-one and 8.21 mL (98.3 mmol) of pyrrolidine in 350 mL CH3OH. After stirring 20 hours at room temperature, the reaction mixture was filtered, washed two times with CH3OH and the precipitate dried under vacuum to give 33.93 of the title product as a yellow powder. Mp: 167°-169° C. 80% yield. 1H NMR (300 m Hz, CDCl3): δ3.93 (s, 3H); 3.91 (s, 3H); 12 aromatic resonances δ6.8→8.1.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washwashed two times with CH3OH
  3. customthe precipitate dried under vacuum

Sources & evidence

ORD record
ord-02213b2da67d4bd1bdc2efb4ca82e803
Source dataset
uspto-grants-1997_06
Patent number
US05641789

Reaction notes

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