HCID 23600236, compound → HCID 67407596, compound

HRID 709854Notes

Reaction equation

HRID 709854 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-0b86ddee8d34447b9b1bdd1491c3bb9c
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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