N-(4-Hydroxyphenyl)Phthalimide → Methyl 7-[4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)phenoxy]-2,2-dimethylheptanoate

HRID 648987노트

반응식

HRID 648987 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]3[C:9]2=[O:18])=[CH:4][CH:3]=1.O(C)[Na].[CH3:22][C:23]([CH3:34])([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]I)[C:24]([O:26][CH3:27])=[O:25]>CN(C=O)C>[O:18]=[C:9]1[C:10]2[C:11](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:13])[N:8]1[C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][C:23]([CH3:22])([CH3:34])[C:24]([O:26][CH3:27])=[O:25])=[CH:7][CH:6]=1

참가 물질

5

반응물 3

HCID 252281N-(4-Hydroxyphenyl)PhthalimideHCID 14153168Methyl 7-iodo-2,2-dimethylheptanoateHCID 178418582HCID 178418582, 화합물

생성물 1

HCID 14153169Methyl 7-[4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)phenoxy]-2,2-dimethylheptanoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N-[p-Hydroxyphenyl]phthalimide (5.0 g) described in Example 1 was dissolved in 100 ml of DMF and 1.13 g of NaOCH3 was added. The solution was stirred at room temperature for one-half hour, then 6.25 g of methyl 2,2-dimethyl-7-iodoheptanoate was added dropwise. The mixture was stirred at room temperature overnight and then heated at reflux for two hours and concentrated on rotary evaporator. H2O (100 ml) was added and a solid was obtained. The product was extracted with EtOAc leaving the insoluble starting material behind. Concentration of the ethyl acetate solution followed by recrystallization of the resulting solid from isopropyl ether gave the purified product; mp 82°-3° C.

후처리

  1. stirringThe mixture was stirred at room temperature overnight
  2. temperatureheated
  3. temperatureat reflux for two hours
  4. concentrationconcentrated on rotary evaporator
  5. additionH2O (100 ml) was added
  6. customa solid was obtained
  7. extractionThe product was extracted with EtOAc leaving the
  8. customConcentration of the ethyl acetate solution followed by recrystallization of the resulting solid from isopropyl ether
  9. customgave the purified product

출처 및 근거

ORD 기록
ord-ecc46022bff34e7b893d5c141d74ad87
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04737512

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