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

HRID 1427363노트

반응식

HRID 1427363 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매2회

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-f1f5ce66f8fc41eda4ac5ac72eb074c5
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933224B2

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