Ethanol → HCID 59191219, compound

HRID 626001Notes

Reaction equation

HRID 626001 reaction equation
[Na].[CH2:2]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11](F)[N:10]=2)=[C:6]([O:18][CH3:19])[CH:5]=1)[CH3:3].[CH2:20]([OH:22])[CH3:21]>>[CH2:20]([O:22][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][C:7]2[CH:16]=[CH:17][C:4]([CH2:2][CH3:3])=[CH:5][C:6]=2[O:18][CH3:19])[N:10]=1)[CH3:21]

Participants

4

Reactant 3

HCID 702EthanolHCID 5360545SodiumHCID 24785925HCID 24785925, compound

Product 1

HCID 59191219HCID 59191219, compound

Conditions

Temperature
80 °C

Procedure

To a solution of sodium (55 mg; 2.39 mmol), under argon, in ethanol (2 mL), was added 2-(4-ethyl-2-methoxyphenoxy)-6-fluoropyridine (82 mg; 0.33 mmol). The reaction was heated to 80° C. for 16 hours then to 90° C. for 26 hours. The mixture was concentrated in vacuo. After quenching with saturated NaHCO3 (10 mL), extractions with ethyl acetate (3*5 mL), the organic phase was dried over NaSO4, and concentrated in vacuo to give the desired product as a light brown oil used without further purification (82 mg; 0.30 mmol; 90%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customAfter quenching with saturated NaHCO3 (10 mL), extractions with ethyl acetate (3*5 mL)
  3. dry with materialthe organic phase was dried over NaSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c549e68f07d4d25a829f965731f24b2
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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