Water → HCID 15483919, compound

HRID 427246Notes

Reaction equation

HRID 427246 reaction equation
[CH3:1][C:2]([CH3:19])([CH3:18])[C:3]#[C:4][C:5]1[CH:6]=[CH:7][C:8]([F:17])=[C:9]([CH:16]=1)[CH2:10][NH:11][C:12](=[O:15])[O:13][CH3:14].[H-].[Na+].[CH3:22][O:23][CH2:24]Br.O>CN(C)C=O>[CH3:1][C:2]([CH3:19])([CH3:18])[C:3]#[C:4][C:5]1[CH:6]=[CH:7][C:8]([F:17])=[C:9]([CH:16]=1)[CH2:10][N:11]([CH2:22][O:23][CH3:24])[C:12](=[O:15])[O:13][CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 83093Bromomethyl methyl etherHCID 15483913methyl N-[5-(3,3-dimethyl-1-butynyl)-2-fluorobenzyl]carbamate

Product 1

HCID 15483919HCID 15483919, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.20 g of methyl N-[5-(3,3-dimethyl-1-butynyl)-2-fluorobenzyl]carbamate was dissolved in N,N-dimethylformamide (5 ml). To this solution, 0.10 g of sodium hydride (60 wt %) was added at room temperature, followed by stirring for 30 minutes. Then, 0.14 g of bromomethyl methyl ether was added at room temperature, followed by stirring for 3 hours. The reaction solution was poured into water and extracted with ethyl acetate, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 0.13 g of methyl N-[5-(3,3-dimethyl-1-butynyl)-2-fluorobenzyl]-N-methoxymethylcarbamate as a colorless viscous liquid.

Workup

  1. stirringby stirring for 3 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a4113585841e49e0a3df9df7a541e53e
Source dataset
uspto-grants-2001_11
Patent number
US06313071B1

Reaction notes

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