Hydrochloric Acid → HCID 58424598, compound

HRID 1408732Notes

Reaction equation

HRID 1408732 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-2604c80bd86d4cc88913cd0911de848e
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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