Ethyl Acetate → HCID 135725108, compound

HRID 993463Notes

Reaction equation

HRID 993463 reaction equation
[C-:1]#[N:2].[Na+].[C:4]([C:8]1[CH:9]=[C:10]([C:19]2[O:20][CH:21]=[C:22]([CH2:24][CH2:25]I)[N:23]=2)[CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])([CH3:7])([CH3:6])[CH3:5].C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.CCCCCC>[C:4]([C:8]1[CH:9]=[C:10]([C:19]2[O:20][CH:21]=[C:22]([CH2:24][CH2:25][C:1]#[N:2])[N:23]=2)[CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 11430Potassium CarbonateHCID 135725039HCID 135725039, compound

Product 1

HCID 135725108HCID 135725108, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolvent

Procedure

To a solution of sodium cyanide (84.5 mmole, 5.50 g) in dimethylsulfoxide (120 ml) at 92° C. was added 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-(2-iodoethyl)oxazole (70.4 mmole, 30.08 g) via a powder addition funnel over an eighty-five minute period. Approximately 1.5 hours later, the reaction was cooled to room temperature and treated with 1:1 ethyl acetate:hexane (250 ml) and 10% aqueous potassium carbonate (250 ml). Three distinct phases result. The lowest phase was separated and discarded. The remaining phases were separated. The aqueous phase was extracted with 1:1 ethyl acetate:hexane (2×200 ml) Combined organic phases were dried over sodium chloride, filtered, reduced in volume and subjected to preparatory chromotography. The material was eluted with 10 to 30% ethyl acetate:hexane. Fractions containing the desired product were combined, dried over MgSO4, filtered and concentrated in vacuo to afford 18.25 g (79%).

Workup

  1. additionvia a powder addition funnel over an eighty-five minute period
  2. customThree distinct phases result
  3. customThe lowest phase was separated
  4. customThe remaining phases were separated
  5. extractionThe aqueous phase was extracted with 1:1 ethyl acetate
  6. dry with materialwere dried over sodium chloride
  7. filtrationfiltered
  8. washThe material was eluted with 10 to 30% ethyl acetate
  9. additionFractions containing the desired product
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customto afford 18.25 g (79%)

Sources & evidence

ORD record
ord-b5ebcabd29644abc95d454fcc3214d01
Source dataset
uspto-grants-2002_10
Patent number
US06472387B1

Reaction notes

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