Ammonium Chloride → HCID 54255094, compound

HRID 1596040

Reaction equation

HRID 1596040 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[Br:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][C:32]=1[CH:41]=O.[Cl-].[NH4+]>C1COCC1>[Br:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][C:32]=1[CH:41]=[CH:2][O:3][CH3:4]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 769091-Bromonaphthalene-2-carbaldehydeHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 54255094HCID 54255094, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (methoxymethyl)triphenyl phosphonium chloride (32.0 g, 93.3 mmol) in THF (100 mL) at −78° C. was treated with potasium tert-butoxide (9.90 g, 88.1 mmol), stirred cold for 1 hour, treated with a solution of 1-bromo-2-naphthaldehyde (12.1 g, 51.7 mmol) (commercially available from TCI America) in THF (75 mL) over 15 minutes, stirred for 16 hours at room temperature, treated with aqueous ammonium chloride (200 mL) and extracted with ethyl acetate. The ethyl acetate was washed with brine, dried (MgSO4), filtered, and concentrated to an oil. The oil was purified on silica gel with a gradient of 2% to 5% ethyl acetate/hexanes to provide 11.8 g (87%) of the desired compound.

Workup

  1. stirringstirred for 16 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customThe oil was purified on silica gel with a gradient of 2% to 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5f5f6e788b304e74abd395907681d3c7
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Linked notes

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