HCID 178418573, compound → HCID 178466675, compound

HRID 656512Notes

Reaction equation

HRID 656512 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[CH3:14][Mg]Br>C1COCC1>[OH:9][CH:8]([C:6]1[N:7]=[C:2]([OH:1])[CH:3]=[C:4]([C:10]([F:13])([F:11])[F:12])[CH:5]=1)[CH3:14]

Participants

4

Reactant 2

HCID 178418573HCID 178418573, compoundHCID 178519650HCID 178519650, compound

Product 1

HCID 178466675HCID 178466675, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

6-hydroxy-4-(trifluoromethyl)picolinaldehyde (2.00 g, 10.5 mmol) was dissolved in dry THF (20 mL) and cooled to −78° C. Methyl magnesium bromide (24 mmol) was added dropwise over 5 minutes. The mixture was allowed to mix for 15 minutes. The reaction was allowed to warm to room temperature and slowly quenched with saturated ammonium chloride (20 mL). The solution was then extracted with ethyl acetate (3×100 mL). The organic extracts were combined and washed with brine (1×) dried over sodium sulfate and concentrated to yield 1.50 g of desired product (70%). 1HNMR (CDCl3 400 MHz) δ6.70 (s, 1H), 6.28 (s, 1H), 4.80 (m, 1H), 3.46 (q, 1H), 1.55 (d, 3H). Mass Spec.: 208.14 (MH)+.

Workup

  1. additionto mix for 15 minutes
  2. temperatureto warm to room temperature
  3. customslowly quenched with saturated ammonium chloride (20 mL)
  4. extractionThe solution was then extracted with ethyl acetate (3×100 mL)
  5. washwashed with brine (1×)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e243b140c9f94b70b7c58c90ad51da91
Source dataset
uspto-grants-2011_12
Patent number
US08071778B2

Reaction notes

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