Hydrochloric Acid → HCID 22279979, compound

HRID 1063418Notes

Reaction equation

HRID 1063418 reaction equation
[C:1]1([C:7]2[C:8](=[O:12])[O:9][CH2:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)(O)[C:15]#[N:16].CN(C)C(=N)N(C)C.Cl>CC#N>[O:12]=[C:8]1[O:9][CH2:10][CH:11]([C:15]#[N:16])[CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6406Acetone CyanohydrinHCID 664601,1,3,3-TetramethylguanidineHCID 109865363-phenyl-2(5H)-furanone

Product 1

HCID 22279979HCID 22279979, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

3-Phenyl-5H-furan-2-one (Description 2; 4.5 g, 0.028 mol), and acetone cyanohydrin (3.06 ml) were dissolved in CH3CN (80 ml) and cooled to −0° C. Tetramethylguanidine (3.5 ml) was added dropwise over 15 minutes and the reaction left to stand for a further 15 minutes. 0.5M HCl (100 ml) was added and the reaction mixture de-colourised and the product extracted with ethyl acetate (2×40 ml), washed with brine (2×30 ml) and dried over MgSO4. The solvent was removed in vacuo to afford a brown oil which was a mixture of the cis and trans isomers. Purification was carried out using flash column chromatography on silica gel eluting in increasing concentrations of ethyl acetate in hexane (0-60%) to yield the title compound (2.93 g, 56%). The only isolated product from the column was the more thermodynamically stable trans isomer.

Workup

  1. waitthe reaction left
  2. extractionthe reaction mixture de-colourised and the product extracted with ethyl acetate (2×40 ml)
  3. washwashed with brine (2×30 ml)
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo
  6. customto afford a brown oil which
  7. additiona mixture of the cis and trans isomers
  8. customPurification
  9. temperaturein increasing concentrations of ethyl acetate in hexane (0-60%)

Sources & evidence

ORD record
ord-b587057e3b3547328394164ecfb4215f
Source dataset
uspto-grants-2005_11
Patent number
US06964981B2

Reaction notes

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