Potassium Sodium Tartrate → 3-Quinolinepropanol

HRID 53219Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][CH2:12][C:13](OCC)=[O:14])[CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>CCOCC>[OH:14][CH2:13][CH2:12][CH2:11][C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution of ethyl 3-(3quinolyl)propionate (1.01 g, 4.4 mmol) in 20 ml of ether was added 2.6 ml (2.6 mmol) of 1M LAH solution at 0° C. After stirring at 0° C. for 15 min, the mixture was allowed to warm and stirred at 20° C. for 3 h, and Rochelle salt (equiv) was added. The mixture was extracted with methylene chloride, and the organic layer was dried over sodium sulfate, and concentrated in vacuo. The residue was purified by chromatography on silica (10 cm column, ethyl acetete/hexane, 1/2-5/1; methylene chloride/acetone, 2/1-1/4) to afford 700 mg (85%) of 3-(3-hydroxypropyl)quinoline, as a thick oil. 3-[3-[4-(5-Trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-quinoline (I, Q=3-quinolyl Y=1,3-propylene, R1,R2 =3,5-dimethyl, R3 =5-trifluoromethyl-1,2,4-oxadiazol-3-yl)

Workup

temperatureto warm
stirringstirred at 20° C. for 3 h
extractionThe mixture was extracted with methylene chloride
dry with materialthe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on silica (10 cm column, ethyl acetete/hexane, 1/2-5/1; methylene chloride/acetone, 2/1-1/4)

Sources & evidence

ORD record: ord-79ea1e225a8f47aa9a9333017b9afbdf
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05618821

Reaction notes

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