Diisopropylamine → HCID 20314652, compound

HRID 462029Notes

Reaction equation

HRID 462029 reaction equation
C(N[CH:5]([CH3:7])[CH3:6])(C)C.C([Li])CCC.[C:13]([O:18][CH3:19])(=[O:17])[CH:14]([CH3:16])[CH3:15].Br[CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([CH2:32]Br)[CH:28]=2)[CH:23]=1>O1CCCC1.CCCCCC>[C:13]([C:5]([CH3:6])([CH3:7])[CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([CH2:32][C:14]([CH3:16])([C:13]([O:18][CH3:19])=[O:17])[CH3:15])[CH:28]=2)[CH:23]=1)([O:18][CH3:19])=[O:17]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 11039Methyl isobutyrateHCID 36600102,6-Bis(bromomethyl)naphthaleneHCID 178418339Butyllithium

Product 1

HCID 20314652HCID 20314652, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 56 ml of diisopropylamine in 1200 ml of dry tetrahydrofuran at -78° C was added 260 ml of 1.6 M n-butyllithium in hexane. After 1 hr of stirring, 40.4 g of methyl isobutyrate was added dropwise and the solution was stirred another 30 minutes. A 60-g portion of 2,6-bis(bromomethyl)naphthalene was added slowly, and the reaction mixture was stirred overnight and then brought to room temperature. Tetrahydrofuran was removed by evaporation. The residue was dissolved in 300 ml of CHCl3, washed 3 times with 400 ml of H2O, and dried and evaporated to dryness to obtain 56 g of 2,6-bis(2-carbomethoxy-2-methylpropyl)naphthalene, m.p. 108°-110° C. The product was recrystallized from benzene.

Workup

  1. stirringthe solution was stirred another 30 minutes
  2. stirringthe reaction mixture was stirred overnight
  3. custombrought to room temperature
  4. customTetrahydrofuran was removed by evaporation
  5. dissolutionThe residue was dissolved in 300 ml of CHCl3
  6. washwashed 3 times with 400 ml of H2O
  7. customdried
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-a80ff6214323423795b3d8d06eda1b26
Source dataset
uspto-grants-1977_12
Patent number
US04065431

Reaction notes

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