Hydrochloric Acid → 2-Methoxy-5-ethyl-6-methylnicotinaldehyde

HRID 2081531ノート

反応式

HRID 2081531 の反応式
[CH3:1][O:2][C:3]1[C:8]([C:9]#N)=[CH:7][C:6]([CH2:11][CH3:12])=[C:5]([CH3:13])[N:4]=1.[H-].C([Al+]CC(C)C)C(C)C.C1C[O:27]CC1.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1.O>[CH3:1][O:2][C:3]1[N:4]=[C:5]([CH3:13])[C:6]([CH2:11][CH3:12])=[CH:7][C:8]=1[CH:9]=[O:27]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 104422282-Methoxy-3-cyano-5-ethyl-6-methylpyridineHCID 86597605diisobutylaluminium hydride THF

生成物 1

HCID 102616792-Methoxy-5-ethyl-6-methylnicotinaldehyde

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-methoxy-3-cyano-5-ethyl-6-methylpyridine (1.0 g, 5.68 mmol) in dry tetrahydrofuran (50 mL) under a nitrogen atmosphere and cooled to -70° C., was added 1.3M diisobutyl aluminum hydride/THF (17.4 mL, 22.7 mmol). The resulting mixture was allowed to warm to room temperature and stir for 15-20 hours. The reaction mixture was acidified with 1N hydrochloric acid and then neutralized with aqueous sodium bicarbonate. Water was then added and the product extracted into diethyl ether. The etheral extract was dried (Na2SO4), filtered and the solvent evaporated. This residue was flash chromatographed on silica gel eluting with 10% diethyl ether/pentane to give the product.

後処理

  1. extractionthe product extracted into diethyl ether
  2. extractionThe etheral extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customchromatographed on silica gel eluting with 10% diethyl ether/pentane
  7. customto give the product

出典と根拠

ORDレコード
ord-f3090cafb0db46b293fc28579f192993
出典データセット
uspto-grants-1993_02
特許番号
US05185251

反応ノート

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