Hydrochloric Acid → HCID 58424598, compound

HRID 2096544Notes

Reaction equation

HRID 2096544 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[CH2:16][CH2:15][C:14](=O)[CH2:13]1.N1CCCC1.Cl>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][C:14]1([CH2:15][CH2:16][O:12][CH2:13]1)[CH2:9][C:8]2=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 5293923-Oxotetrahydrofuran

Product 1

HCID 58424598HCID 58424598, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (4.97 g, 23.23 mmol), dihydrofuran-3(2H)-one (3 g, 34.87 mmol) and pyrrolidine (2.48 g, 34.87 mmol) in toluene (60 mL) was refluxed overnight. After cooling, the mixture was treated with water and acidified with concentrated HCl to pH around 1. The resulting solution was extracted with ethyl acetate and washed with brine. The combined organic layers were concentrated and the residue was purified by column to give 6-bromo-4′,5′-dihydro-2′H-spiro[chroman-2,3′-furan]-4-one (1.7 g, 30%). 1H-NMR (CDCl3): 1.9 (m, 1H), 2.3 (m, 1H), 2.8 (m, 2H), 3.65 (m, 1H), 3.9 (m, 1H), 4.0 (m, 2H), 6.8 (m, 1H), 7.5 (m, 1H), 7.9 (m, 1H).

Workup

  1. temperatureAfter cooling
  2. extractionThe resulting solution was extracted with ethyl acetate
  3. washwashed with brine
  4. concentrationThe combined organic layers were concentrated
  5. customthe residue was purified by column

Sources & evidence

ORD record
ord-3ac229e50a9e48e9a9e359cd424b66eb
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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