Water → 2,2-dibutyl-3,4-dihydro-5-(2-quinolylmethoxy)-1(2H)-naphthalenone

HRID 1650218Notes

Reaction equation

[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH2:2]1.Cl[CH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.[C:24](=[O:27])([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:10]([C:7]1([CH2:6][CH2:4][CH2:5][CH3:6])[CH2:8][CH2:9][C:10]2[C:5](=[CH:4][CH:3]=[CH:2][C:1]=2[O:11][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[C:24]1=[O:27])[CH2:1][CH2:2][CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2,2-dibutyl-3,4-dihydro-5-hydroxy-(1(2H)-naphthalenone (2.643 g), 2-chloromethylquinoline (1.7 g), and potassium carbonate (1.67 g) in N,N-dimethylformamide (16 ml) was stirred at 80° C. for 4 hours. The cooled mixture was poured into water. The separated oil was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried, and concentrated in vacuo. The crude product was chromatographed on silica gel using 25% ethyl acetate in n-hexane as eluent to yield 2,2-dibutyl-3,4-dihydro-5-(2-quinolylmethoxy)-1(2H)-naphthalenone (3.09 g) as a pale yellow syrup.

Workup

extractionThe separated oil was extracted with ethyl acetate
washThe ethyl acetate layer was washed with water
customdried
concentrationconcentrated in vacuo
customThe crude product was chromatographed on silica gel using 25% ethyl acetate in n-hexane as eluent

Sources & evidence

ORD record: ord-6d07b49f6a414a27840cd3cde1ef3e89
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04923881

Reaction notes

Loading…