Allyl bromide → HCID 22459145, compound

HRID 613414Notes

Reaction equation

HRID 613414 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-6c5cc08f9c32426981945587fc7ac224
Source dataset
uspto-grants-1999_12
Patent number
US06008237

Reaction notes

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