Sodium hydride → 1-(4-Fluorostyryl)naphthalene

HRID 1694769Notes

Reaction equation

HRID 1694769 reaction equation
[C:1]1([CH2:11][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[F:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=1>C1COCC1>[F:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=[CH:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 2734114(Naphthalen-1-ylmethyl)triphenylphosphonium

Product 1

HCID 27964071-(4-Fluorostyryl)naphthalene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

An oven-dried 500 ml three-neck flask was purged with nitrogen and charged with (naphthalen-1-ylmethyl)triphenylphosphonium (11.67 g, 26.6 mmol) and dry THF (200 ml). Sodium hydride (1.06 g, 26.6 mmol) was added and reaction mixture was left to stir overnight at room temperature. Solution was orange in the morning. A solution of 4-fluorobenzaldehyde (3.0 g, 24.2 mmol) in dry THF (30 ml) was added next day (16 h later) over the period of 45 minutes, bleaching the orange-red color. Reaction mixture was stirred at room temperature for 24 hours. THF was removed under reduced pressure. Crude product was purified by column chromoatography on silica gel with 5% CHCl3 in hexanes. The desired product is a mixture of cis- and trans-isomers. Yield 5.7 g (95%) of a viscous oil. The structure was confirmed by 1H NMR spectroscopy.

Workup

  1. customAn oven-dried 500 ml three-neck flask was purged with nitrogen
  2. customreaction mixture
  3. waitwas left
  4. customReaction mixture
  5. stirringwas stirred at room temperature for 24 hours
  6. customTHF was removed under reduced pressure
  7. customCrude product was purified by column chromoatography on silica gel with 5% CHCl3 in hexanes
  8. additiona mixture of cis- and trans-isomers

Sources & evidence

ORD record
ord-078036bbd5834835a8a56446729cb9c0
Source dataset
uspto-grants-2012_04
Patent number
US08158831B2

Reaction notes

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