2,4-Dichlorobenzyl chloride → HCID 87735234, compound

HRID 2253250Notes

Reaction equation

HRID 2253250 reaction equation
[O:1]([CH3:11])[CH:2]1[O:8][C@@H:7]([CH2:9][OH:10])[C@@H:5]([OH:6])[C@@H:3]1[OH:4].[H-].[Na+].[Cl:14][C:15]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=1[CH2:17]Cl>CO>[Cl:14][C:15]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=1[CH2:17][O:4][C@H:3]1[C@H:5]([O:6][CH2:17][C:16]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:15]=2[Cl:14])[C@H:7]([CH2:9][O:10][CH2:17][C:16]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:15]=2[Cl:14])[O:8][CH:2]1[O:1][CH3:11]

Participants

5

Reactant 3

HCID 72122,4-Dichlorobenzyl chlorideHCID 24758Sodium hydride2×HCID 12042993methyl L-xylofuranoside

Product 1

HCID 87735234HCID 87735234, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 1-1 from Step A is dissolved in anhydrous TBF and the solution is cooled in an ice bath. To the cold solution is added sodium hydride (60% dispersion in mineral oil) and the reaction mixture is stirred for 35 to 45 min under an argon atmosphere. To this mixture is added 2,4-dichlorobenzyl chloride slowly over 20 min. The reaction mixture is stirred for 72 h, then cooled in an ice bath. MeOH is added slowly to decompose excess NaH. The mixture is concentrated under reduced pressure and the residue is taken up in ethyl acetate and washed several times with water. The organic layer is dried over anhydrous Na2SO4, filtered, and evaporated. The residue is purified by silica gel chromatography using a mixture of hexane and ethyl acetate as the eluent. The appropriate fractions are combined and evaporated to afford compound 1-2.

Workup

  1. temperaturethe solution is cooled in an ice bath
  2. stirringThe reaction mixture is stirred for 72 h
  3. temperaturecooled in an ice bath
  4. concentrationThe mixture is concentrated under reduced pressure
  5. washwashed several times with water
  6. dry with materialThe organic layer is dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by silica gel chromatography
  10. additiona mixture of hexane and ethyl acetate as the eluent
  11. customevaporated

Sources & evidence

ORD record
ord-f8674037e9fa4bb3ab88eb96a704f2be
Source dataset
uspto-grants-2008_01
Patent number
US07323449B2

Reaction notes

Loading…