Tetrahydrofuran → HCID 66598296, compound

HRID 899605Notes

Reaction equation

HRID 899605 reaction equation
[PH4+].[H-].[Na+].[NH:4]1[CH:8]=[CH:7][C:6]([CH:9]=O)=[N:5]1.[NH4+:11].[Cl-].[CH2:13]1[CH2:17]OCC1>>[N:4]1[NH:5][C:6]([CH:9]=[CH:17][C:13]#[N:11])=[CH:7][CH:8]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 5460504PhosphoniumHCID 122183831H-Pyrazole-3-carbaldehyde

Product 1

HCID 66598296HCID 66598296, compound

Procedure

To a suspension of the phosphonium salt (900 mg, 2.35 mmol) in THF (10 mL) under nitrogen was added NaH (60% in mineral oil, 99 mg, 2.5 mmol) in one portion. The suspension stirred at room temperature for 10 minutes, then pyrazole-3-carboxaldehyde (211 mg, 2.20 mmol) was added as a solid in one portion. The reaction was heated to reflux for 30 minutes, then cooled to room temperature and saturated aqueous NH4Cl (10 mL) was added. The mixture was extracted with CH2Cl2 (25 mL×3) and the combined organic solution was dried (MgSO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (EtOAc/hexane, 1:1) gave the alkene (white solid) as an approximately 1.5:1 mixture of the E:Z isomers (232 mg, 1.95 mmol, 89%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 30 minutes
  3. temperaturecooled to room temperature
  4. extractionThe mixture was extracted with CH2Cl2 (25 mL×3)
  5. dry with materialthe combined organic solution was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash column chromatography on silica (EtOAc/hexane, 1:1)

Sources & evidence

ORD record
ord-cdcfb133cd3443cc9954a0921cf5b102
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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