Hydrochloric Acid → HCID 86724260, compound

HRID 873718Notes

Reaction equation

HRID 873718 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.[CH3:12][CH:13]([CH3:17])[CH2:14][CH:15]=O.N1CCCC1.Cl>CCOC(C)=O.CO>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][CH:15]([CH2:14][CH:13]([CH3:17])[CH3:12])[CH2:9][C:8]2=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 115523-MethylbutanalHCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 86724260HCID 86724260, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-(5-bromo-2-hydroxyphenyl)ethanone (10.0 g, 46.5 mmol) and MeOH (0.20 L) were added 3-methylbutanal (7.54 mL, 69.8 mmol) and pyrrolidine (5.77 mL, 69.8 mmol) at ambient temperature, and the mixture was stirred for 3 days at the same temperature. After concentration of the reaction mixture at reduced pressure, the residue was diluted with EtOAc, acidified to pH 3-4 with 1M aqueous HCl, and extracted with EtOAc. The organic layer was washed with water and brine, dried over MgSO4, and filtered. After concentration of the filtrate at reduced pressure, purification of the residue with column chromatography on silica gel (EtOAc-hexane, a linear gradient of EtOAc from 0 to 10%) afforded 6-bromo-2-isobutyl-2,3-dihydro-4H-chromen-4-one (9.02 g).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customAfter concentration of the filtrate at reduced pressure, purification of the residue with column chromatography on silica gel (EtOAc-hexane

Sources & evidence

ORD record
ord-43c4739c3f7b45c08cad1f7ac4155794
Source dataset
uspto-grants-2015_03
Patent number
US08975415B2

Reaction notes

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