Allyl bromide → HCID 22459145, compound

HRID 1532163Notes

Reaction equation

HRID 1532163 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[C:13]3[CH:14]=[CH:15][C:16]([OH:18])=[CH:17][C:12]=3[S:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19](Br)[CH:20]=[CH2:21].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]1([CH2:7][CH2:8][C:9]2[C:13]3[CH:14]=[CH:15][C:16]([O:18][CH2:21][CH:20]=[CH2:19])=[CH:17][C:12]=3[S:11][CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 22459064HCID 22459064, compound

Product 1

HCID 22459145HCID 22459145, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of the product from Step E (4.651 grams) in dry DMF (40 mL) was exposed to allyl bromide (1.66 mL) followed by cesium carbonate (6.26 grams). After 2.5 hours at ambient temperature, the reaction was partitioned between isopropyl acetate and pH4 pthalate buffer. The organic was washed twice with water, dried over magnesium sulfate and filtered. Evaporation gave a residue which, when chromatographed over silica gel (3:1 hex/CH2Cl2), gave the title compound, a clear oil.

Workup

  1. customthe reaction was partitioned between isopropyl acetate and pH4
  2. washThe organic was washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customEvaporation
  6. customgave a residue which, when
  7. customchromatographed over silica gel (3:1 hex/CH2Cl2)

Sources & evidence

ORD record
ord-6b88e7779ebe46c9a8fab992b3421e81
Source dataset
uspto-grants-2001_03
Patent number
US06200998B1

Reaction notes

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