Benzyl Alcohol → HCID 12180874, compound

HRID 1196223Notes

Reaction equation

HRID 1196223 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][C:6](=[O:16])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:17](O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.Cl>O1CCCC1.CCOCC.C(OC(=O)C)C>[CH3:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:5]=[CH:4][N:3]=1

Participants

9

Reactant 5

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 27264163-(BENZYLOXY)-2-METHYL-4(1H)-PYRIDINONEHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 12180874HCID 12180874, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 154.8 g of the product of Example 2, 86.4 g benzylalcohol and 210 g triphenylphosphine suspended in 1.5 liters (dry) tetrahydrofurane was added a solution of 139.2g diethylazodicarboxylate in 500 ml tetrahydrofuran within 20 minutes. The temperature rose to 53° C. for several hours. After 4.5 hours a clear solution was obtained. After standing overnight, a solution of HCl in ether (28 g) was added. Hydrochlorides of Example 3 and 3 A crystallized from the solution. After cooling they were isolated by filtration and washed with ether and petroleum ether. 230 g of the mixture of HCL salts of 3 and 3A was suspended in 2 liters of ethyl acetate and 1 liter of water. The pH was adjusted to 7.0 with concentrated NaOH solution. The organic phase and two organic was phases were combined and dried over Na2SO4. Filtration and distilling off the solvent yielded an oily residue which was passed through a column with 600 g SiO2. Ethylacetate as eluent. Only the title compound of Example 3B, 151.8 g, was eluted from the column. Eluation of 3A is possible with CH3OH. M.P.=92° C. (title comp. 3)

Workup

  1. waitThe temperature rose to 53° C. for several hours
  2. customAfter 4.5 hours a clear solution was obtained
  3. customHydrochlorides of Example 3 and 3 A crystallized from the solution
  4. temperatureAfter cooling they
  5. customwere isolated by filtration
  6. washwashed with ether and petroleum ether
  7. dry with materialdried over Na2SO4
  8. filtrationFiltration
  9. distillationdistilling off the solvent
  10. customyielded an oily residue which
  11. washOnly the title compound of Example 3B, 151.8 g, was eluted from the column

Sources & evidence

ORD record
ord-fa315175eed74bdc89249c157f5df5be
Source dataset
uspto-grants-1992_05
Patent number
US05112968

Reaction notes

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