Dimethylformamide → HCID 117940185, compound

HRID 62283Notes

Reaction equation

HRID 62283 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][CH:3]=1.[Li]CCCC.CN([CH:26]=[O:27])C>C1COCC1>[F:10][C:9]([F:12])([F:11])[C:8]([C:6]1[N:7]=[C:2]([CH:26]=[O:27])[CH:3]=[CH:4][CH:5]=1)([OH:17])[C:13]([F:16])([F:15])[F:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 19426938HCID 19426938, compoundHCID 178418339Butyllithium

Product 1

HCID 117940185HCID 117940185, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 261 (0.5 g, 1.54 mmol) in dry THF, cooled to 0° C., n-BuLi (0.118 g, 1.85 mmol) was added drop wise and continued stirring for 10 min. Then DMF (0.224 g, 3.08 mmol) was added to the reaction mixture while stirring for another 2 h. After completion of the reaction, it was quenched with saturated ammonium chloride solution. The organic layer was separated and aqueous phase was extracted again with diethyl ether, the combined organic layer was dried over sodium sulphate and concentrated to get the crude compound 6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)picolinaldehyde 262.

Workup

  1. stirringwhile stirring for another 2 h
  2. customAfter completion of the reaction, it
  3. customwas quenched with saturated ammonium chloride solution
  4. customThe organic layer was separated
  5. extractionaqueous phase was extracted again with diethyl ether
  6. dry with materialthe combined organic layer was dried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ae52165577554b9e8e1df278fdd9f65b
Source dataset
uspto-grants-2016_09
Patent number
US09446047B2

Reaction notes

Loading…