Hexane → HCID 18786339, compound

HRID 1108084Notes

Reaction equation

HRID 1108084 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:17]C)[CH:5]=[C:6]([C:8]2([C:13]([O:15][CH3:16])=[O:14])[CH2:12][CH:11]=[CH:10][CH2:9]2)[CH:7]=1.B(Br)(Br)Br.C[Si](C=[N+]=[N-])(C)C.CCCCCC>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([OH:17])[CH:5]=[C:6]([C:8]2([C:13]([O:15][CH3:16])=[O:14])[CH2:9][CH:10]=[CH:11][CH2:12]2)[CH:7]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 25134Boron tribromideHCID 167693TrimethylsilyldiazomethaneHCID 18786343HCID 18786343, compound

Product 1

HCID 18786339HCID 18786339, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of methyl 1-(5-fluoro-3-methoxyphenyl)cyclopent-3-ene-1-carboxylate (495 mg, 2.0 mmol) in dry dichloromethane (10 ml) was added a 1.0M solution of boron tribromide in dichloromethane (10 ml, 10 mmol) at -78° C. and the mixture stirred for 1 hr at the same temperature. The reaction mixture was quenched by the addition of water (20 ml) and the resulted mixture acidified with 1.0N aqueous hydrochloric acid, and extracted with ethyl acetate. The organic phase was washed with brine, dried and concentrated under reduced pressure. The residue was dissolved in a mixture of methanol (5 ml) and toluene (15 ml) and a 2.0M solution of trimethylsilyldiazomethane in hexane (2 ml, 4 mmol) was added at ambient temperature with stirring. After 0.5 hr, the reaction mixture was partitioned between ethyl acetate and water, the organic phase was separated and the aqueous phase was extracted with ethyl acetate. The combined organic phase was washed with brine, dried with MgSO4 and concentrated in vacuo. The resultant oil was purified by column chromatography (SiO2, 150 g; hexane/ethyl acetate (4/1)) to afford 407 mg (87%) of methyl 1-(5-fluoro-3-hydroxyphenyl)cyclopent-3-ene-1-carboxylate white crystals.

Workup

  1. customThe reaction mixture was quenched by the addition of water (20 ml)
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in a mixture of methanol (5 ml) and toluene (15 ml)
  7. stirringwith stirring
  8. waitAfter 0.5 hr
  9. customthe reaction mixture was partitioned between ethyl acetate and water
  10. customthe organic phase was separated
  11. extractionthe aqueous phase was extracted with ethyl acetate
  12. washThe combined organic phase was washed with brine
  13. dry with materialdried with MgSO4
  14. concentrationconcentrated in vacuo
  15. customThe resultant oil was purified by column chromatography (SiO2, 150 g; hexane/ethyl acetate (4/1))

Sources & evidence

ORD record
ord-c53dd159b9e6452398f01a92a851fcdb
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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