Ethyl 4,6-dichloro-2-methylnicotinate → (4,6-Dichloro-2-methylpyridin-3-yl)methanol

HRID 590769ノート

反応式

HRID 590769 の反応式
[Cl:1][C:2]1[C:7]([C:8](OCC)=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]([Cl:14])[CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([Cl:14])[N:5]=[C:6]([CH3:13])[C:7]=1[CH2:8][OH:9]

参加物

5

反応物 3

HCID 2786748Ethyl 4,6-dichloro-2-methylnicotinateHCID 9855836Potassium sodium tartarateHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 118168968(4,6-Dichloro-2-methylpyridin-3-yl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

THF (52.3 mL) was cooled to 0° C. in a dry round bottomed flask under an atmosphere of N2. Ethyl 4,6-dichloro-2-methylnicotinate (4.60 mL, 26.1 mmol) was then added followed by diisobutylaluminum hydride (57.5 mL, 57.5 mmol). The reaction was stirred at 0° C. for 3 h. The reaction was then poured into cold saturated sodium potassium tartrate solution. The mixture was stirred for several hours to allow the precipitate to dissolve, then the aqueous phase was extracted with EtOAc. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (0-50% EtOAc/hexanes) to give (4,6-dichloro-2-methylpyridin-3-yl)methanol. MS ESI calc'd. for C7H7Cl2NO [M+1]+ 192. found 192.

後処理

  1. stirringThe mixture was stirred for several hours
  2. dissolutionto dissolve
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (0-50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-86d7ad49606748bea40370da620da2e4
出典データセット
uspto-grants-2016_01
特許番号
US09233979B2

反応ノート

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