Gamma-Butyrolactone → 4-Hydroxy-1-(2-naphthyl)-1-butanone

HRID 2229250Notes

Reaction equation

HRID 2229250 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[Li]CCCC.[C:17]1(=[O:22])[O:21][CH2:20][CH2:19][CH2:18]1.[NH4+].[Cl-]>C1COCC1.CCCCCC>[OH:22][CH2:17][CH2:18][CH2:19][C:20]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1)=[O:21]

Participants

7

Reactant 4

HCID 7302Gamma-ButyrolactoneHCID 113722-BromonaphthaleneHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 184670444-Hydroxy-1-(2-naphthyl)-1-butanone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled (−78° C.) solution of 2-bromonaphthalene (10.77 g) in THF (150 ml) was added n-BuLi in hexane (1.65M, 36 ml) and the mixture was stirred at −78° C. for 30 minutes. To the solution was added γ-butyrolactone (25 ml) and the mixture was stirred at −78° C. for 1 minute. Aqueous solution of NH4Cl was added and the mixture was extracted with ethyl acetate. The extract was washed with aqueous NH4Cl solution, water and brine, dried and concentrated. The residue was chromatographed on silica gel (hexane:ethyl acetate=3:1) followed by recrystallization from cyclohexane-ethyl acetate to give the titled compound (6.71 g) as a colorless solid.

Workup

  1. stirringthe mixture was stirred at −78° C. for 1 minute
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with aqueous NH4Cl solution, water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (hexane:ethyl acetate=3:1)
  7. customfollowed by recrystallization from cyclohexane-ethyl acetate

Sources & evidence

ORD record
ord-3a2a7b57dbe9461c8a11e1ab97deb6dc
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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