Potassium Hydroxide → 2-[(4-Fluorophenyl)methyl]heptanedioic acid

HRID 326008노트

반응식

HRID 326008 반응식
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12])=[O:5])C.[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.[O-:22]CC.[Na+].[OH-].[K+]>C(O)C.O>[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][CH:6]([C:4]([OH:3])=[O:5])[CH2:11][CH2:10][CH2:9][CH2:8][C:7]([OH:12])=[O:22])=[CH:16][CH:15]=1

참가 물질

7

반응물 4

HCID 14797Potassium HydroxideHCID 680214-Fluorobenzyl bromideHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 2723922Sodium ethoxide

생성물 1

HCID 135197692-[(4-Fluorophenyl)methyl]heptanedioic acid수율 87.6%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

19.2 g of 2-oxocyclohexanecarboxylic acid ethyl ester, 21.4 g of p-fluorobenzyl bromide, 7.7 g of sodium ethoxide and 200 ml of ethanol were mixed together to form a mixture which was refluxed for 2 hours, incorporated with 500 ml of water and subjected to extraction with ethyl ether. The resulting ether layer was freed of the ether to obtain a residue. The thus obtained residue was dissolved in 500 ml of 70% ethanol, incorporated with 16.1 g of potassium hydroxide, refluxed for 3 hours and hydrolyzed to obtain 26.5 g of 1-(4-fluorobenzyl)-1,5-pentane dicarboxylic acid having a melting point of 80°-81° C. in the colorless needle form. 26 g of the thus obtained compound in the needle form and 300 g of polyphosphoric acid were mixed together to form a mixture which was agitated at 100° C. for 3 hours. After the end of the reaction, the resulting reaction mixture was incorporated with iced water and subjected to extraction with ethyl acetate. The organic layer was washed with water, dehydrated and freed of the solvent by distilling it off, thereby to obtain a residue. The thus obtained residue was recrystallized from isopropyl ether to obtain 18.2 g of 6-fluoro-1-oxo-2,3-dihydro-2-indene valeric acid in the colorless platy form.

후처리

  1. customto form a mixture which
  2. extractionsubjected to extraction with ethyl ether
  3. customto obtain a residue
  4. temperaturerefluxed for 3 hours

출처 및 근거

ORD 기록
ord-8c2c92b7eb6048f18bafb815685ead19
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04443626

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