Diisopropylamine → HCID 22959237, compound

HRID 2303457Notes

Reaction equation

HRID 2303457 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[O:13]1[CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]2[CH2:15][C:14]1=[O:22].Br[CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1>C1COCC1.O>[CH:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:33]=[CH:34][C:25]=1[CH2:24][CH:15]1[CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[O:13][C:14]1=[O:22]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 703202-BromomethylnaphthaleneHCID 95391Hexahydro-3H-benzofuran-2-oneHCID 178418339Butyllithium

Product 1

HCID 22959237HCID 22959237, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

Under argon, a solution of diisopropylamine (3.36 ml, 24 mmol) in 20 ml of dry THF was cooled to 0° C. and admixed with butyllithium (9.6 ml, 24 mmol, 2.5 M in hexane). The solution was stirred with ice-cooling for 15 min, cooled to −78° C. and admixed with a solution of hexahydro-benzofuran-2-one (2.8 g, 20 mmol) in 10 ml of THF. This mixture was stirred at −78° C. for 1 h, and a solution of 2-bromomethylnaphthalene (5.31 g, 24 mmol) in 20 ml of THF was then added. The mixture was stirred at −78° C. for another 2 h and then at room temperature overnight. Water was then added, the organic solvent was removed under reduced pressure and the aqueous phase was extracted with MTBE. The combined ether phases were dried over magnesium sulphate, filtered and concentrated. Purification was carried out by column chromatography. Yield: 2.5 g (44.6%). Rf (cyclohexane/ethyl acetate 3:1)=0.69, Rf (cyclohexane/ethyl acetate 1:1)=0.83 MS (CI): m/e=281 [M+H+]

Workup

  1. temperaturecooling for 15 min
  2. stirringThis mixture was stirred at −78° C. for 1 h
  3. stirringThe mixture was stirred at −78° C. for another 2 h
  4. customat room temperature
  5. customovernight
  6. customthe organic solvent was removed under reduced pressure
  7. extractionthe aqueous phase was extracted with MTBE
  8. dry with materialThe combined ether phases were dried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification

Sources & evidence

ORD record
ord-a58557930a03424da5b721dd456302c9
Source dataset
uspto-grants-2002_08
Patent number
US06433004B1

Reaction notes

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