Tetrahydrofuran → HCID 86014539, compound

HRID 2253145Notes

Reaction equation

HRID 2253145 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:6]=1[CH:18](Br)Br)[CH3:2].[O:22]1CCCC1>O.[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:6]=1[CH:18]=[O:22])[CH3:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 66713124HCID 66713124, compound

Product 1

HCID 86014539HCID 86014539, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Procedure

2-Dibromomethyl-4-phenoxy-benzoic acid ethyl ester (2.07 g) was dissolved in tetrahydrofuran (40 mL) and water (15 mL). Silver nitrate (2.56 g) was added. The resulting mixture was heated to reflux for 5 h. The precipitate was filtered off and the reaction was diluted with ethyl acetate. The organic layer was separated and the aqueous layer was extracted again with ethyl acetate. The combined ethyl acetate layer was washed with saturated sodium bicarbonate solution, brine, and dried with magnesium sulfate. After concentration, the crude oil was diluted with 20% ethyl acetate in hexanes (100 mL) and filtered through a pad of silica gel. Further rinse was continued twice. The filtrate solution was concentrated to give the title compound 1.13 g as an oil. 1H NMR (200 MHz, CDCl3) δ 10.62 (s, 1H), 7.98 (d, J=8.6 Hz, 1H), 7.42-7.35 (m, 3H), 7.20-7.14 (m, 2H), 7.04 (d, J=8.2, 2H), 4.41 (q, J=7.0 Hz, 2H), 1.41 (t, J=7.0 Hz, 3H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 5 h
  3. filtrationThe precipitate was filtered off
  4. additionthe reaction was diluted with ethyl acetate
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted again with ethyl acetate
  7. washThe combined ethyl acetate layer was washed with saturated sodium bicarbonate solution, brine
  8. dry with materialdried with magnesium sulfate
  9. concentrationAfter concentration
  10. additionthe crude oil was diluted with 20% ethyl acetate in hexanes (100 mL)
  11. filtrationfiltered through a pad of silica gel
  12. washFurther rinse
  13. concentrationThe filtrate solution was concentrated

Sources & evidence

ORD record
ord-55a205c718d743d88927b2c42fb562f1
Source dataset
uspto-grants-2008_01
Patent number
US07323475B2

Reaction notes

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