Tetrahydrofuran → HCID 58270306, compound

HRID 2362610Notes

Reaction equation

HRID 2362610 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([CH:16]=[O:17])=[CH:11][CH:10]=2.[CH2:18]1COCC1.C[Mg]Br>>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([CH:16]([OH:17])[CH3:18])=[CH:11][CH:10]=2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 58270237HCID 58270237, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58270306HCID 58270306, compound

Conditions

Temperature
-78 °C

Procedure

1-(3-(2-methoxyethoxy quinolin-6-yl)ethanol. 3-(2-methoxyethoxy)quinoline-6-carbaldehyde (1.7 g, 7.4 mmol) was dissolved in THF (29 mL, 7.4 mmol) and cooled to −78° C. To the solution was added methylmagnesium bromide (7.4 mL, 22 mmol), and the reaction was allowed to warm to RT. After 1 h, the reaction was quenched with sat. aq ammonium chloride. The material was extracted with DCM (×3) and the combined organics were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was then purified via MPLC (eluting with 0-100% 90:10:1 DCM:MeOH:NH4OH in DCM). 1-(3-(2-methoxyethoxy)quinolin-6-yl)ethanol was obtained.

Workup

  1. temperatureto warm to RT
  2. customthe reaction was quenched with sat. aq ammonium chloride
  3. extractionThe material was extracted with DCM (×3)
  4. dry with materialthe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was then purified via MPLC (eluting with 0-100% 90:10:1 DCM:MeOH:NH4OH in DCM)

Sources & evidence

ORD record
ord-af9e233ab9aa4c1b80ff25332e733303
Source dataset
uspto-grants-2014_04
Patent number
US08691838B2

Reaction notes

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