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

HRID 1189837ノート

反応式

HRID 1189837 の反応式
[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]

参加物

4

反応物 2

HCID 21225700DiisobutylaluminumhydrideHCID 45116302Ethyl 5-nitropicolinate

生成物 1

HCID 20583228(5-Nitropyridin-2-yl)methanol収率 29.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]−.

後処理

  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)

出典と根拠

ORDレコード
ord-c8e8f76f72e8416b811a30a374cdb0e3
出典データセット
uspto-grants-2014_03
特許番号
US08674099B2

反応ノート

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