Pyrrolidine → HCID 58424460, compound

HRID 2096642Notes

Reaction equation

HRID 2096642 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[OH:11])(=[O:3])[CH3:2].[O:12]1[CH2:17][CH2:16][CH2:15][C:14](=O)[CH2:13]1.N1CCC[CH2:20]1>CO>[Br:10][C:8]1[CH:9]=[C:4]2[C:5](=[CH:6][C:7]=1[CH3:20])[O:11][C:14]1([CH2:15][CH2:16][CH2:17][O:12][CH2:13]1)[CH2:2][C:1]2=[O:3]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 901092H-Pyran-3(4H)-one, dihydro-HCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 58424460HCID 58424460, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-Acetyl-4-bromophenol (920 mg, 4.02 mmol), dihydro-2H-pyran-3(4H)-one (402 mg, 4.02 mmol) and pyrrolidine (0.5 mL) in MeOH (10 mL) was heated to reflux for 2 h. The reaction mixture was cooled down to room temperature and evaporated. The residue was purified by flash chromatography on silica gel eluting with EA in hexane (0-20%) to give 6-bromo-7-methyl-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-one (593 mg); MS ESI +ve m/z 311 (M+H)+.

Workup

  1. temperatureto reflux for 2 h
  2. customevaporated
  3. customThe residue was purified by flash chromatography on silica gel eluting with EA in hexane (0-20%)

Sources & evidence

ORD record
ord-f80d777ee992495ab8aff840a0be37c7
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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