1-Chloromethylnaphthalene → HCID 19089934, compound

HRID 1463282Notes

Reaction equation

HRID 1463282 reaction equation
[H-].[Na+].[OH:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[H][H].[C:14]1([CH2:24]Cl)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1>CN(C)C=O.O>[C:14]1([CH2:24][O:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 68451-ChloromethylnaphthaleneHCID 24758Sodium hydrideHCID 97534tert-butyl N-hydroxycarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 19089934HCID 19089934, compoundYield 38.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, a suspension of 1.6 grams (0.041 mole) of 60% sodium hydride (in mineral oil) in dimethylformamide was stirred, and 5.4 grams (0.041 mole) of 1,1-dimethylethyl N-hydroxycarbamate was carefully added portionwise. Upon completion of the evolution of hydrogen, 5.8 grams (0.032 mole) of naphth-1-ylmethyl chloride was added. Upon completion of addition, the reaction mixture was stirred for about 30 minutes. After this time the reaction mixture was poured into 200 ml of water. The mixture was extracted with 200 ml of diethyl ether. The ether extract was washed with three 50 ml portions of water. The organic layer was concentrated under reduced pressure to a residual oil. The oil was purified by column chromatography on silica gel. Elution was accomplished with mixtures of 5% to 20% diethyl ether in petroleum ether. The appropriate fractions were combined and concentrated under reduced pressure, yielding 3.4 grams of 1,1-dimethylethyl N-(naphth-1-ylmethoxy)carbamate. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. stirringthe reaction mixture was stirred for about 30 minutes
  3. extractionThe mixture was extracted with 200 ml of diethyl ether
  4. extractionThe ether extract
  5. washwas washed with three 50 ml portions of water
  6. concentrationThe organic layer was concentrated under reduced pressure to a residual oil
  7. customThe oil was purified by column chromatography on silica gel
  8. washElution
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d645cff9d16d42a5836dea8e1cdbf62a
Source dataset
uspto-grants-1994_04
Patent number
US05300503

Reaction notes

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