Sodium Cyanide → HCID 19764560, compound

HRID 248058Notes

Reaction equation

HRID 248058 reaction equation
[CH3:1][C:2]([CH3:22])([O:4][C:5](=[O:21])[CH2:6][S:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:20])[C:16]([O:18]C)=[O:17])=[CH:10][CH:9]=1)[CH3:3].[C-]#N.[Na+]>CN(C)P(N(C)C)(N(C)C)=O.[Cl-].[NH4+]>[CH3:22][C:2]([CH3:3])([O:4][C:5](=[O:21])[CH2:6][S:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:20])[C:16]([OH:18])=[O:17])=[CH:10][CH:9]=1)[CH3:1]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 86746789HCID 86746789, compound

Product 1

HCID 19764560HCID 19764560, compound

Reagents, catalysts & solvents 2

HCID 12679HexamethylphosphoramideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
70 °C

Procedure

Dissolve 4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]thio]-alpha-methyl-benzenepropanoic acid, methyl ester (10.5 g, 32.4 mmol) in anhydrous hexamethylphos-phoramide (160 mL) and treat with sodium cyanide (1.59 g, 32.4 mmol). Heat at 70° C. for 48 hours, cool and dilute with saturated ammonium chloride (300 mL). Extract with ethyl ether (400 mL), wash with water (2×300 mL), then brine (300 mL) and dry (MgSO4). Evaporate the solvent in vacuo and purify by flash chromatography to give the title compound.

Workup

  1. temperaturecool
  2. extractionExtract with ethyl ether (400 mL)
  3. washwash with water (2×300 mL)
  4. dry with materialbrine (300 mL) and dry (MgSO4)
  5. customEvaporate the solvent in vacuo
  6. custompurify by flash chromatography

Sources & evidence

ORD record
ord-5a1663f6934b46469f87b09df6aa3fa6
Source dataset
uspto-grants-1993_05
Patent number
US05208240

Reaction notes

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