Chloride → HCID 13409052, compound

HRID 2166850Notes

Reaction equation

HRID 2166850 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[BH4-].[Na+].Cl.S(Cl)(Cl)=O.[Cl-].[C-:29]#[N:30].[Na+]>O.C(O)C.C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:9]([Cl:10])=[C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[CH2:4][C:29]#[N:30]

Participants

10

Reactant 6

HCID 312ChlorideHCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 24386Thionyl ChlorideHCID 4311764Sodium borohydrideHCID 13409048HCID 13409048, compound

Product 1

HCID 13409052HCID 13409052, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

To a suspension of the compound from Example 25, (20.9 g., 0.067 mole) in 125 ml. of absolute ethanol was added 0.79 g. (0.021 mole) of NaBH4. The mixture was stirred for 20 minutes at room temperature. The reaction mixture was diluted by careful addition of water and was then acidified with dilute HCl. The ethanol was evaporated under reduced pressure and the aqueous residue was extracted with methylene chloride. The organic solution was washed with brine, dried over Na2SO4 and evaporated to provide 20 g. of benzylic alcohol. This alcohol (20 g., 0.064 mole) was dissolved in 150 ml. of chloroform and 18.7 ml. of thionyl chloride was added. After the solution had been stirred for 5 hours at room temperature, the solvent was evaporated to give 21.1 g. of benzylic chloride. NMR (CDCl3): 4.70 (2H, s, ArCH2Cl). This chloride (21.1 g., 0.064 mole) was dissolved in 150 ml. of 95% ethanol and a solution of NaCN (3.74 g., 0.076 mole) in 25 ml. of water was added. The mixture was refluxed for 8 hours. The ethanol was evaporated and the aqueous residue was extracted with methylene chloride. The organic extract was washed with brine, dried over Na2SO4 and evaporated. The crude product was quickly passed through a short silica gel column using methylene chloride as the solvent. The desired product (16.6 g.) was obtained as a yellow solid. NMR (CDCl3): 3.93 (2H, s, ArCH2CN); IR (CHCl3) 2250 cm-1.

Workup

  1. customThe ethanol was evaporated under reduced pressure
  2. extractionthe aqueous residue was extracted with methylene chloride
  3. washThe organic solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customto provide 20 g
  7. stirringAfter the solution had been stirred for 5 hours at room temperature
  8. customthe solvent was evaporated
  9. customto give 21.1 g
  10. temperatureThe mixture was refluxed for 8 hours
  11. customThe ethanol was evaporated
  12. extractionthe aqueous residue was extracted with methylene chloride
  13. extractionThe organic extract
  14. washwas washed with brine
  15. dry with materialdried over Na2SO4
  16. customevaporated

Sources & evidence

ORD record
ord-91f8d4f0713e47b3ae3f2a78fcc543c9
Source dataset
uspto-grants-1983_06
Patent number
US04389416

Reaction notes

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