Pyrrolidine → HCID 58423954, compound

HRID 1408684Notes

Reaction equation

HRID 1408684 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[O:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.N1CCCC1>CO>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][C:15]1([CH2:16][CH2:17][O:12][CH2:13][CH2:14]1)[CH2:9][C:8]2=[O:10]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 121599Tetrahydro-4H-pyran-4-one

Product 1

HCID 58423954HCID 58423954, compoundYield 108.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (10 g, 46.7 mmol), dihydro-2H-pyran-4(3H)-one (9.35 g, 93.45 mmol) and pyrrolidine (6.3 g, 88.8 mmol) in methanol (200 mL) was stirred overnight. The reaction mixture was removed in vacuo, and H2O was added. The resulting solution was extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4, filtered, and evaporated to give 6-bromo-2′,3′,5′,6′-tetrahydrospiro[chroman-2,4′-pyran]-4-one (15 g, 100%). 1HNMR (CDCl3): 1.74 (m, 2H), (m, 2H), 1.94 (t, 2H), 2.71 (s, 2H), 3.76 (m, 4H), 6.91 (d, 1H), 7.54 (d, 1H), 7.96 (s, 1H).

Workup

  1. customThe reaction mixture was removed in vacuo, and H2O
  2. additionwas added
  3. extractionThe resulting solution was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1cfe35e8d1524c009620ea7a65062105
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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