Dimethylformamide → 3-Pyridinecarboxaldehyde, 5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-

HRID 62281ノート

反応式

HRID 62281 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[N:6][CH:7]=1.C([Mg]Cl)(C)C.CN([CH:26]=[O:27])C>C1COCC1>[F:10][C:9]([F:12])([F:11])[C:8]([C:4]1[CH:5]=[N:6][CH:7]=[C:2]([CH:3]=1)[CH:26]=[O:27])([OH:17])[C:13]([F:16])([F:15])[F:14]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 177589312-(5-Bromopyridin-3-yl)-1,1,1,3,3,3-hexafluoropropan-2-olHCID 178418918HCID 178418918、化合物

生成物 1

HCID 177581373-Pyridinecarboxaldehyde, 5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 258 (0.347 g, 1.07 mmol) in dry THF, cooled to 0° C., was added isopropyl magnesium chloride (1.2 mL, 2.4 mmol) drop wise and stirred for 10 min followed by the addition of DMF (0.015 ml, 1.94 mmol) to the reaction and stirred for additional 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 5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)nicotinaldehyde 259 used directly to proceed for the next step.

後処理

  1. stirringstirred for additional 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

出典と根拠

ORDレコード
ord-3190a22fa8d24b61b45f88707785f2ac
出典データセット
uspto-grants-2016_09
特許番号
US09446047B2

反応ノート

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