Ethyl Acetate → HCID 135725108, compound

HRID 1279926Notes

Reaction equation

HRID 1279926 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 eightyfive 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 100 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 eightyfive 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 materialCombined organic phases were 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-9c9dea28cfbd4e2390e5da9101aa18f7
Source dataset
uspto-grants-2002_09
Patent number
US06448396B2

Reaction notes

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