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

HRID 590769노트

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HRID 590769 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-86d7ad49606748bea40370da620da2e4
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233979B2

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