Sodium hydride → 1-(4-Fluorostyryl)naphthalene

HRID 1912031Notes

Reaction equation

HRID 1912031 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-10bc3269cca8479f9ad862cee3e48fb1
Source dataset
uspto-grants-2013_12
Patent number
US08604247B2

Reaction notes

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