3-Fluorobenzaldehyde → HCID 11345075, compound

HRID 1823834Notes

Reaction equation

HRID 1823834 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])C=CC=CC=1>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4](/[CH:5]=[CH:17]/[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 680093-FluorobenzaldehydeHCID 256127tert-Butyl (triphenylphosphoranylidene) acetate

Product 1

HCID 11345075HCID 11345075, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-fluorobenzaldehyde (10 g, 80 mmol) in tetrahydrofuran (370 ml) was added tert-butyl 2-(triphenylphosphoranylidene)acetate (27.6 g, 73.3 mmol) in 1 g portions over 30 minutes. Upon final addition, the mixture was heated to reflux for 10 minutes. The solvent was removed under reduced pressure. The white waxy residue was triturated with pentane (x2). The pentane extracts were combined and evaporated under reduced pressure. The residue was purified by filtration through a plug of silica gel using an eluent of diethyl ether:hexane (1:2) to afford the title compound as a colorless oil, 16.2 g.

Workup

  1. additionUpon final addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 10 minutes
  4. customThe solvent was removed under reduced pressure
  5. customThe white waxy residue was triturated with pentane (x2)
  6. customevaporated under reduced pressure
  7. filtrationThe residue was purified by filtration through a plug of silica gel using an eluent of diethyl ether:hexane (1:2)

Sources & evidence

ORD record
ord-65ea52f0553042fca803e6f893383c51
Source dataset
uspto-grants-2006_05
Patent number
US07041667B1

Reaction notes

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