1-Chloromethylnaphthalene → HCID 54143623, compound

HRID 976047Notes

Reaction equation

HRID 976047 reaction equation
[H-].[Na+].[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].Cl[CH2:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1>C1COCC1>[C:20]1([CH2:19][CH:4]([C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6])[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 68451-ChloromethylnaphthaleneHCID 24758Sodium hydrideHCID 68324Di-tert-butyl malonate

Product 1

HCID 54143623HCID 54143623, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

A suspension of 5.96 g (0.124 mol) of NaH.oil (50%) was washed with THF to remove the oil, then suspended in 450 mL THF. Di-t-butyl malonate (25.4 mL, 0.113 mol) was then added causing a mild exotherm. The solution was heated to reflux for 45 minutes, then cooled to 30° C. A solution of 20.0 g (0.113 mol) of 1-chloromethylnaphthalene in 50 mL THF was then added and the solution heated at reflux for 3 hours, then left stirring overnight. The mixture was filtered and the filtrate removed under reduced pressure. The residue was taken up in EtOAc and washed with 1N citric acid, saturated NaCl, saturated NaHCO3, then saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left 39.65 g (98.4% yield) of the product as an oil.

Workup

  1. washoil (50%) was washed with THF
  2. customto remove the oil
  3. temperatureThe solution was heated
  4. temperatureto reflux for 45 minutes
  5. temperaturethe solution heated
  6. temperatureat reflux for 3 hours
  7. waitleft
  8. filtrationThe mixture was filtered
  9. customthe filtrate removed under reduced pressure
  10. washwashed with 1N citric acid, saturated NaCl, saturated NaHCO3
  11. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-75055d3cc1f4416fbf0b8384353c0955
Source dataset
uspto-grants-1997_03
Patent number
US05610177

Reaction notes

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