Allyl bromide → HCID 22459145, compound

HRID 2185049Notes

Reaction equation

HRID 2185049 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-110164de943d4586948a8d26b712f654
Source dataset
uspto-grants-2002_06
Patent number
US06399640B1

Reaction notes

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