Sodium hydride → HCID 23226370, compound

HRID 1005583Notes

Reaction equation

HRID 1005583 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[S:8].[H-].[Na+].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][O:1][CH2:2][CH2:3][CH2:4][C:5]2[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=2[C:7]([O:9][CH3:10])=[S:8])=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 53767092HCID 53767092, compound

Product 1

HCID 23226370HCID 23226370, compoundYield 39.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice bath cooled solution of methyl 2-(3-hydroxyprop-1-yl)thiobenzoate (3.7 g) in N,N-dimethylformamide (30 ml) was added sodium hydride (60% in oil, 719 mg) and the solution was stirred at the same temperature for 30 minutes. 4-Methoxybenzyl chloride (2.56 g) was added to the solution and the mixture was stirred at ambient temperature for 5 hours. The mixture was diluted with ethyl acetate (100 ml) and the solution was washed with water and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo to give a crude oil. The crude product was purified by silica gel column chromatography (hexane: ethyl acetate=10:1) to give methyl 2-[3-(4-methoxyphenyl)methoxyprop-1-yl]thiobenzoate (2.13 g).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 5 hours
  2. washthe solution was washed with water and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customto give a crude oil
  6. customThe crude product was purified by silica gel column chromatography (hexane: ethyl acetate=10:1)

Sources & evidence

ORD record
ord-3193057644d6414faf5107946fecd96d
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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