Allyl bromide → HCID 20034695, compound

HRID 231198Notes

Reaction equation

HRID 231198 reaction equation
[CH:1]([N-]C(C)C)([CH3:3])[CH3:2].[Li+].C([Li])(C)(C)C.C(NC(C)C)(C)C.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:33][C:34]([CH2:36][C:37]2[CH:42]=[C:41]([O:43][CH3:44])[C:40]([O:45][CH3:46])=[C:39]([O:47][CH3:48])[CH:38]=2)=[O:35])[CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30].C(Br)C=C>CCCCC.O1CCCC1.O>[CH2:3]([CH:33]([C:25]1[CH:26]=[C:27]([O:31][CH3:32])[C:28]([O:29][CH3:30])=[C:23]([O:22][CH3:21])[CH:24]=1)[C:34]([CH2:36][C:37]1[CH:38]=[C:39]([O:47][CH3:48])[C:40]([O:45][CH3:46])=[C:41]([O:43][CH3:44])[CH:42]=1)=[O:35])[CH:1]=[CH2:2]

Participants

9

Reactant 5

HCID 7841Allyl bromideHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 20034702HCID 20034702, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 20034695HCID 20034695, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of lithium diisopropylamide (prepared from the addition of 38.2 ml of a 1.7M solution of tert.-butyl lithium in pentane to 9.53 ml of diisopropylamine in 100 ml of tetrahydrofuran at -10° C.) which was cooled to -78° C. was slowly added 24.1 g of the compound prepared in (c) above in 450 ml of tetrahydrofuran. The resultant mixture was then stirred for 45 minutes, while maintaining the temperature of -78° C., after which time it was cannulated into a solution of 159 ml of allyl bromide in 244 ml of tetrahydrofuran at -78° C. over a period of 90 minutes. The reaction mixture was then stirred for an additional 30 minutes at -78° C., after which time it was allowed to warm to room temperature. 150 ml of water was then added and the tetrahydrofuran was removed by evaporation at 40° C. The crude residue was then extracted with a mixture of ethyl acetate and water and dried, after which time the organic fraction was evaporated to yield a solid.

Workup

  1. temperaturewhile maintaining the temperature of -78° C.
  2. temperatureto warm to room temperature
  3. customthe tetrahydrofuran was removed by evaporation at 40° C
  4. extractionThe crude residue was then extracted with a mixture of ethyl acetate and water
  5. customdried
  6. customafter which time the organic fraction was evaporated
  7. customto yield a solid

Sources & evidence

ORD record
ord-6bffac06a67e4686b82663e98f2acc82
Source dataset
uspto-grants-1989_07
Patent number
US04845129

Reaction notes

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