Benzyl Bromide → HCID 10060973, compound

HRID 478037Notes

Reaction equation

HRID 478037 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7])[CH3:2].[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:10])[CH:5]([S:6]([CH3:9])(=[O:8])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 78201Ethyl methanesulfonylacetate

Product 1

HCID 10060973HCID 10060973, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

6.648 g of methylsulphonyl-acetic acid ethyl ester in 20 ml of DMF are added dropwise at -25°, within 25 minutes, to 1.745 g of sodium hydride dispersion (55% in oil) in 40 ml of DMF. The solution is subsequently stirred for 30 minutes at -25°, then 6.84 g of benzyl bromide in 40 ml of DMF are added dropwise. The reaction mixture is then stirred for 1 hour at room temperature, left to stand overnight and concentrated by evaporation. The residue is taken up in ethyl acetate, washed with water, dried, concentrated by evaporation and purified by flash chromatography on 700 g of silica gel 60 (eluant E). 1H-NMR (DMSO-d6): 1.1 ppm (t, 3H); 3.05 (s, 3H), 3.1-3.6 (m, 2H); 3.9-4.3 (m, 3H); 7.25 (m, 5H).

Workup

  1. stirringThe reaction mixture is then stirred for 1 hour at room temperature
  2. waitleft
  3. waitto stand overnight
  4. concentrationconcentrated by evaporation
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated by evaporation
  8. custompurified by flash chromatography on 700 g of silica gel 60 (eluant E)

Sources & evidence

ORD record
ord-573018a20a15454db97a2b16826354d7
Source dataset
uspto-grants-1989_12
Patent number
US04889869

Reaction notes

Loading…