Benzyl Alcohol → HCID 178517844, compound

HRID 478063Notes

Reaction equation

HRID 478063 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:12][C:13]1[N:14]=[C:15]([OH:23])[C:16]2[S:22][CH2:21][CH2:20][CH2:19][C:17]=2[N:18]=1>C1COCC1.CN(C=O)C>[CH2:3]([O:10][CH2:12][C:13]1[N:14]=[C:15]([OH:23])[C:16]2[S:22][CH2:21][CH2:20][CH2:19][C:17]=2[N:18]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 178517759HCID 178517759, compound

Product 1

HCID 178517844HCID 178517844, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.68 g 53% mineral oil) was suspended in THF (80 ml) and 1.5 ml of benzyl alcohol was added dropwise with stirring. To this clear solution was added product from Example 3, Step A (2.6 g) dissolved in 25 ml of DMF. After stirring for 2 hours at 25° C. the reaction mixture was heated at reflux for 10 minutes. The solvent was removed in vacuo, water was added to the residue followed by enough diluted HCl to render the solution slightly acidic and it was extracted with ethyl acetate. The ethyl acetate layer was dried and evaporated to give title compound as an oil that was used directly in Step B.

Workup

  1. stirringAfter stirring for 2 hours at 25° C. the reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 10 minutes
  4. customThe solvent was removed in vacuo, water
  5. additionwas added to the residue
  6. extractionit was extracted with ethyl acetate
  7. dry with materialThe ethyl acetate layer was dried
  8. customevaporated

Sources & evidence

ORD record
ord-96bdf4459cc14f4fad9759e6700381b3
Source dataset
uspto-grants-1989_12
Patent number
US04889856

Reaction notes

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