4-Chlorobenzyl alcohol → HCID 13176479, compound

HRID 1006476Notes

Reaction equation

HRID 1006476 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6].[CH:14]1[C:19]([CH2:20]O)=[CH:18][CH:17]=[C:16]([Cl:22])[CH:15]=1.C(P(CCCC)CCCC)CCC>O1CCCC1>[Cl:22][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][O:1][C:2]2[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=2)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 133974-Chlorobenzyl alcoholHCID 13831TributylphosphineHCID 218653763-hydroxy-N-methoxy-N-methylbenzamide

Product 1

HCID 13176479HCID 13176479, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.81 g (10.0 mmol) B5, 1.57 g (11.0 mmol) 4-chlorobenzylic alcohol and 3.03 g (15.0 mmol) tributylphosphine were dissolved in 100 ml tetrahydrofurane and 3.78 g (15.0 mmol) azodicarbonylpiperidine was added at 10° C. The mixture was stirred at room temperature overnight. After removal of the precipitate, the mother liquor was evaporated to dryness and the residue was taken up with ethyl acetate. After filtration and washing with aqueous sodium hydrogen carbonate, 2 N HCl and water, the organic phase was dried over sodium sulfate end the solvent was removed in vacuo. Chromatography of the residue on SiGel (n-heptane/ethyl acetate 2:1) yielded 2.8 g (90%) B8.

Workup

  1. customAfter removal of the precipitate
  2. customthe mother liquor was evaporated to dryness
  3. filtrationAfter filtration
  4. washwashing with aqueous sodium hydrogen carbonate, 2 N HCl and water
  5. dry with materialthe organic phase was dried over sodium sulfate end the solvent
  6. customwas removed in vacuo

Sources & evidence

ORD record
ord-68bd7cab173f46438adf84effeabfc41
Source dataset
uspto-grants-2004_09
Patent number
US06790852B2

Reaction notes

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