Diisobutylaluminumhydride → (5-Nitropyridin-2-yl)methanol

HRID 43151노트

반응식

HRID 43151 반응식
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=1)=O)C>C(Cl)Cl>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([CH2:14][OH:13])=[N:17][CH:18]=1)([O-:24])=[O:23]

참가 물질

4

반응물 2

HCID 21225700DiisobutylaluminumhydrideHCID 45116302Ethyl 5-nitropicolinate

생성물 1

HCID 20583228(5-Nitropyridin-2-yl)methanol수율 29.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Diisobutylaluminium hydride (1 M in DCM, 41.6 mL, 41.6 mmol, 1.3 equiv) was added dropwise to a cold (−78° C.) solution of 5-nitro-pyridine-2-carboxylic acid ethyl ester (Step 39.4) (6.4 g, 32 mmol) in DCM (120 mL), under an argon atmosphere. The reaction mixture was allowed to warm to rt, quenched by addition of an aqueous solution of potassium sodium tartrate, diluted with DCM and H2O, and filtered through a pad of celite. The filtrate was extracted several times with DCM. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 9:1→1:1) to provide 1.44 g of the title compound: ESI-MS: 153.1 [M−H]−.

후처리

  1. customquenched by addition of an aqueous solution of potassium sodium tartrate
  2. additiondiluted with DCM and H2O
  3. filtrationfiltered through a pad of celite
  4. extractionThe filtrate was extracted several times with DCM
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 9:1→1:1)

출처 및 근거

ORD 기록
ord-062a8fa1bf754846b758e3effd466d29
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536175B2

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