Benzyl Alcohol → HCID 178517844, compound

HRID 982138Notes

Reaction equation

HRID 982138 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH2:11].Cl.Cl.CO[CH2:16][C:17]1[N:18]=[C:19](N2CCNCC2)[C:20]2[S:26][CH2:25][CH2:24][CH2:23][C:21]=2[N:22]=1>C1COCC1.CN(C=O)C>[CH2:3]([O:10][CH2:16][C:17]1[N:18]=[C:19]([OH:11])[C:20]2[S:26][CH2:25][CH2:24][CH2:23][C:21]=2[N:22]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 20068697HCID 20068697, 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-2b7ad0f879a7480491a3fca9f66c6b27
Source dataset
uspto-grants-1991_02
Patent number
US04994464

Reaction notes

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