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

HRID 1256197

반응식

HRID 1256197 반응식
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]

참가 물질

5

반응물 3

HCID 13387N-methyl-2-pyrrolidoneHCID 37055Methyl 2,4-dichlorobenzoateHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 66741803Methyl 2,4-diethylbenzoate수율 32%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-df7fc28527434d7ea26309fb34a639e8
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461153B2

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