Methyl 5-methyl-3-oxohexanoate → Methyl 5-methyl-2-nitro-3-oxohexanoate

HRID 931353ノート

反応式

HRID 931353 の反応式
[N:1]([O-:3])=[O:2].[Na+].[CH3:5][CH:6]([CH3:15])[CH2:7][C:8](=[O:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11]>O.C(O)(=O)C>[CH3:5][CH:6]([CH3:15])[CH2:7][C:8](=[O:14])[CH:9]([N+:1]([O-:3])=[O:2])[C:10]([O:12][CH3:13])=[O:11]

参加物

5

反応物 2

HCID 121701Methyl 5-methyl-3-oxohexanoateHCID 23668193Sodium Nitrite

生成物 1

HCID 42609287Methyl 5-methyl-2-nitro-3-oxohexanoate

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒2 回

実験手順

A solution of sodium nitrite (232 g, 3.36 mol) in water (560 mL) was added drop-wise over 1.5 hours to a solution of methyl 5-methyl-3-oxohexanoate (400 g, 2.53 mol) in glacial acetic acid (510 mL) at 20 to 25° C. Stirring was continued at room temperature for 2 hours. Water (1.3 L) was added, and the reaction mixture was stirred for an additional 18 hours. The mixture was then extracted with ethyl acetate (3×2.5 L), and the combined organic layers were washed sequentially with water (2.5 L), with aqueous sodium bicarbonate solution (2.5 L), and with saturated aqueous sodium chloride solution (1.0 L). After drying over sodium sulfate, the organic extracts were concentrated in vacuo to afford the product as a yellow liquid, which was used directly in the next step. Yield: 456 g, 2.24 mol, 89%.

後処理

  1. stirringthe reaction mixture was stirred for an additional 18 hours
  2. extractionThe mixture was then extracted with ethyl acetate (3×2.5 L)
  3. washthe combined organic layers were washed sequentially with water (2.5 L), with aqueous sodium bicarbonate solution (2.5 L)
  4. dry with materialAfter drying over sodium sulfate
  5. concentrationthe organic extracts were concentrated in vacuo

出典と根拠

ORDレコード
ord-9d2e5ba3772c4588a8501e7003267432
出典データセット
uspto-grants-2016_03
特許番号
US09296761B2

反応ノート

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