N-methyl-2-pyrrolidone → Methyl 2,4-diethylbenzoate

HRID 409375

反応式

HRID 409375 の反応式
Cl[C:2]1[CH:11]=[C:10](Cl)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CN1CC[CH2:16][C:15]1=O.[CH2:20]([Mg]Br)[CH3:21]>O1CCCC1>[CH2:15]([C:2]1[CH:11]=[C:10]([CH2:20][CH3:21])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH3:16]

参加物

5

反応物 3

HCID 13387N-methyl-2-pyrrolidoneHCID 37055Methyl 2,4-dichlorobenzoateHCID 178418443HCID 178418443、化合物

生成物 1

HCID 66741803Methyl 2,4-diethylbenzoate収率 32%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of Fe(acac)3 (0.34 g, 0.96 mmol), methyl 2,4-dichlorobenzoate (4.0 g, 19.6 mmol), and N-methyl-2-pyrrolidinone (8 mL) in THF (100 mL) at −20° C. under nitrogen was added a tetrahydrofuran (THF) solution (1.0 M) of ethylmagnesium bromide (40.0 mL, 40.0 mmol) over a period of −5 min. The resulting mixture was stirred while gradually warming to ambient temperature. Stirring was continued for an additional 17 h. The reaction mixture was partitioned between water and dichloromethane. The organic layer was separated, washed with brine, dried (MgSO4), and pumped to dryness under reduced pressure. The brown residue was purified by column chromatography (SiO2, 20% EtOAc/heptane) to give 1.2 g of the desired product as a clear oil (yield of 32%), along with 1.1 g of methyl 4-ethylbenzoate. 1H NMR (300 MHz, DMSO-d6) δ 1.15 (t, 3H), 1.20 (t, 3H), 2.66 (q, 2H), 2.92 (q, 2H), 3.82 (s, 3H), 7.15 (d, 1H), 7.23 (s, 1H), 7.76 (d, 1H).

後処理

  1. stirringStirring
  2. customThe reaction mixture was partitioned between water and dichloromethane
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customThe brown residue was purified by column chromatography (SiO2, 20% EtOAc/heptane)

出典と根拠

ORDレコード
ord-1a3a7c50a19442639d8110e26465a844
出典データセット
uspto-grants-2014_06
特許番号
US08759340B2

関連ノート

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