HCID 23600236, compound → HCID 67407596, compound

HRID 1802070Notes

Reaction equation

HRID 1802070 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([CH:19]=[O:20])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:21][Mg]I>C1COCC1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([CH:19]([OH:20])[CH3:21])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 23600236HCID 23600236, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 67407596HCID 67407596, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(heptyloxy)quinoline-3-carbaldehyde (1.6 g, 5.9 mmol) in THF (30 mL) at 0° C. was added CH3MgI (2 g, 12 mmol, 2 eq.) dropwise over 10 min. The mixture was warmed to it over 8 h. Then, the reaction mixture was quenched (water), extracted (ethyl acetate), washed (brine), dried (Na2SO4), filtered and evaporated to dryness to give the crude product, which was purified by silica gel column chromatography (pet. ether:ethyl acetate, 1:5) to give 1-(7-(heptyloxy)quinolin-3-yl)ethanol as yellow oil (1.35 g, yield 80%). ESI-MS: 288 (M+H)+.

Workup

  1. temperatureThe mixture was warmed to it over 8 h
  2. customThen, the reaction mixture was quenched (water)
  3. extractionextracted (ethyl acetate)
  4. washwashed (brine)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customto give the crude product, which
  9. customwas purified by silica gel column chromatography (pet. ether:ethyl acetate, 1:5)

Sources & evidence

ORD record
ord-eb9be36591ce48839d233cefacacceaa
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

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