1-Iodohexane → 2(1H)-Quinolinone, 6-acetyl-1-hexyl-3,4-dihydro-4,4-dimethyl-

HRID 1840873Notes

Reaction equation

[H-].[Na+].[C:3]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][C:9]2([CH3:18])[CH3:17])(=[O:5])[CH3:4].I[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CN(C=O)C>[CH2:20]([N:12]1[C:13]2[C:8](=[CH:7][C:6]([C:3](=[O:5])[CH3:4])=[CH:15][CH:14]=2)[C:9]([CH3:18])([CH3:17])[CH2:10][C:11]1=[O:16])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (21 mg, 90 mmol) was slowly added into a solution of 6-acetyl-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (Intermediate 5, 98 mg, 45 mmol) in 3 mL of DMF at 0° C. After stirring at 0° C. for 10 min, 1-iodo-n-hexane (29 mg, 135 mmol) was added to the reaction mixture and the ice-bath was removed. The reaction was allowed to stir for 2 h before quenching with ice water. The resulting solution was then extracted with ether (3×10 mL), washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (75:25 hexane/ethyl acetate) yielded the title compound as a colorless oil (41.8 mg, 31% yield).

Workup

customthe ice-bath was removed
stirringto stir for 2 h
custombefore quenching with ice water
extractionThe resulting solution was then extracted with ether (3×10 mL)
washwashed with brine (1×10 mL)
dry with materialdried (MgSO4)
concentrationconcentrated at reduced pressure
customPurification by flash chromatography (75:25 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-618af945b3e5410287c4ed2e02da2b5d
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06683092B1

Reaction notes

Loading…