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N-methyl-2-pyrrolidone → Methyl 4-(prop-2-enyl)-2-(2-methylphenyl)benzoate

HRID 383132
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HRID 383132 반응식
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH:3]=1.[CH2:19]([Sn](CCCC)(CCCC)CCCC)[CH:20]=[CH2:21].CN1C(=O)CCC1>C1(C)C=CC=CC=1.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:21]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH:3]=1)[CH:20]=[CH2:19]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 13387N-methyl-2-pyrrolidoneHCID 90628AllyltributylstannaneHCID 11508596HCID 11508596, 화합물

생성물 1

HCID 18361425Methyl 4-(prop-2-enyl)-2-(2-methylphenyl)benzoate수율 74%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매
HCID 1140
Toluene
용매
HCID 8857Ethyl Acetate용매

실험 절차

Methyl 4-iodo-2-(2-methylphenyl)benzoate (10.0 g, 28.4 mmol), allyltributyl tin (11.3 g, 34.1 mmol), and dichlorobis(triphenylphosphine)palladium (II) (1.0 g, 1.42 mmol) were combined in 50 mL toluene and 20 mL NMP and heated at 125° C. for 18 hours. The reaction was diluted with EtOAc, washed with water and brine, dried over Na2SO4, and chromatographed (5% EtOAc in hexanes) to provide the title compound in 74 % yield. MS m/e 284 (M+NH4)+.

후처리

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customchromatographed (5% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-c80cfb0bb8ec48d098d5413a923f3aab
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06310095B1

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