Ethyl Acetate → HCID 15229921, compound

HRID 1769386Notes

Reaction equation

HRID 1769386 reaction equation
FC(F)(F)S(O[C:7]1[C:15]([CH2:16]/[CH:17]=[C:18](\[CH3:25])/[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:14]([O:26][CH3:27])[C:13]([CH3:28])=[C:12]2[C:8]=1[C:9](=[O:29])[O:10][CH2:11]2)(=O)=O.[C-:32]#[N:33].[K+].C(OCC)(=O)C>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:32]([C:7]1[C:15]([CH2:16]/[CH:17]=[C:18](\[CH3:25])/[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:14]([O:26][CH3:27])[C:13]([CH3:28])=[C:12]2[C:8]=1[C:9](=[O:29])[O:10][CH2:11]2)#[N:33]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 15229920HCID 15229920, compound

Product 1

HCID 15229921HCID 15229921, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A nitrogen-flushed mixture of 5.8 g (12.4 retool) of methyl (E)-6-(1,3-dihydro-4-trifluoromethylsulfonyloxy -6-methoxy-7-methyl-3-oxoisobenzofuran5-yl)-4-methyl-4-hexenoate, 1.5 g (23.0 mmol) of potassium cyanide, and 1.11 g (0.96 mmol) of tetrakis(triphenylphosphine) palladium in 100 ml of 1,4-dioxane was heated at reflux for 18 hours. Upon cooling, the mixture was partitioned between water and ethyl acetate. The organic phase was washed with water six times, with brine once, and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the resulting solid was stirred with hexane for 18 hours and then filtered off. This solid was further purified by silica gel chromatography using 5:4 hexane:ethyl acetate to give 4.0 g (11.7 mmol) of methyl (E)-6-(1,3-dihydro-4-cyano-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4hexenoate, mp 87°-88° C.

Workup

  1. customA nitrogen-flushed
  2. temperaturewas heated
  3. temperatureat reflux for 18 hours
  4. temperatureUpon cooling
  5. customthe mixture was partitioned between water and ethyl acetate
  6. washThe organic phase was washed with water six times, with brine once
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. filtrationfiltered off
  10. customThis solid was further purified by silica gel chromatography

Sources & evidence

ORD record
ord-7d20785cd80342d7a43a519b9ced47f8
Source dataset
uspto-grants-1995_01
Patent number
US05380879

Reaction notes

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