Diisopropylamine → HCID 22995662, compound

HRID 1167101Notes

Reaction equation

HRID 1167101 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[C:13]1([CH:19]([CH2:25][CH3:26])[CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Br:27][CH2:28][CH2:29][CH2:30]Br>CCCCCC.O1CCCC1>[Br:27][CH2:28][CH2:29][CH2:30][C:19]([CH2:25][CH3:26])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:20][C:21]([O:23][CH3:24])=[O:22]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 80011,3-DibromopropaneHCID 578303HCID 578303, compoundHCID 178418339Butyllithium

Product 1

HCID 22995662HCID 22995662, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-10 °C

Procedure

15 g (0.081 mol) of n-butyl lithium as a 2.5-molar solution in hexane are added dropwise to a solution of 11.35 ml (0.081 mol) of diisopropylamine in 200 ml of anhydrous tetrahydrofuran at −30° C. and stirred for 10 minutes at −10° C. 14.4 g (0.081 mol) of methyl 2-phenylbutanecarboxylate are added dropwise at −76° C. and stirred for 30 minutes at this temperature. Then 8.62 ml (0.085 mol) of 1,3-dibromopropane are added, when the addition has ended the cooling bath is removed and the mixture is stirred for 14 hours at ambient temperature. The reaction solution is poured onto 1.2 l of water and extracted with diethylether. The organic phases are extracted with water, dried over sodium sulphate and the solvent is eliminated. The residue is distilled under high vacuum.

Workup

  1. stirringstirred for 30 minutes at this temperature
  2. additionwhen the addition
  3. customis removed
  4. stirringthe mixture is stirred for 14 hours at ambient temperature
  5. additionThe reaction solution is poured onto 1.2 l of water
  6. extractionextracted with diethylether
  7. extractionThe organic phases are extracted with water
  8. dry with materialdried over sodium sulphate
  9. distillationThe residue is distilled under high vacuum

Sources & evidence

ORD record
ord-ec855913fe94486fab008e3569dfe25c
Source dataset
uspto-grants-2003_09
Patent number
US06617325B1

Reaction notes

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