Pyrrolidine → HCID 58424225, compound

HRID 1408752Notes

Reaction equation

HRID 1408752 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:15](=[O:17])[CH3:16].[O:18]1[CH2:23][CH2:22][CH2:21][C:20](=O)[CH2:19]1.N1CCCC1>C1(C)C=CC=CC=1>[O:8]([C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[O:1][C:20]1([CH2:21][CH2:22][CH2:23][O:18][CH2:19]1)[CH2:16][C:15]2=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 901092H-Pyran-3(4H)-one, dihydro-HCID 12264993HCID 12264993, compound

Product 1

HCID 58424225HCID 58424225, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-(2-hydroxy-5-phenoxyphenyl)ethanone (2.0 g, 8.77 mmol) in toluene (30 mL) was added dihydro-2H-pyran-3(4H)-one (1.14 g, 11.40 mmol) and pyrrolidine (0.81 g, 11.40 mmol), and the reaction mixture was refluxed overnight. After cooling, the mixture was concentrated. The residue was washed with 1 N HCl, brine, dried and concentrated to give the crude product, which was purified by chromatography to afford 6-phenoxy-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-one (1.40 g, 52%). 1H-NMR (CDCl3): 0.79 (m, 1H), 1.52 (m, 2H), 1.67 (m, 1H), 1.92 (m, 1H), 2.08 (m, 1H), 2.57-2.61 (q, 2H), 3.51 (m, 2H), 3.88 (m, 2H), 6.89 (d, 2H), 7.03 (m, 2H), 7.18 (m, 1H), 7.26 (t, 2H), 7.39 (m, 1H).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. washThe residue was washed with 1 N HCl, brine
  5. customdried
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas purified by chromatography

Sources & evidence

ORD record
ord-2eea46c8830e4dc8b52cc85b6e027392
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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