Sodium Cyanide → 4-[[2-(1,1-Dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid

HRID 248054Notes

Reaction equation

HRID 248054 reaction equation
[CH3:1][C:2]([CH3:22])([O:4][C:5](=[O:21])[CH2:6][O: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][O: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 867467874-[[2-(1,1-Dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid, methyl ester

Product 1

HCID 197645314-[[2-(1,1-Dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acidYield 11.4%

Reagents, catalysts & solvents 2

HCID 12679HexamethylphosphoramideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
70 °C

Procedure

Dissolve 4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid, methyl ester (10 g, 32.4 mmol) in anhydrous hexamethylphosphoramide (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 (5→10% methanol/chloroform) to give the title compound (1.09 g).

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 (5→10% methanol/chloroform)

Sources & evidence

ORD record
ord-d900912d80b7425b8daab391bfe570f0
Source dataset
uspto-grants-1993_05
Patent number
US05208240

Reaction notes

Loading…