Hydrochloric Acid → 4''-Diethylamino-3''-ethyl-4'-(3-hydroxypropoxy)-[1,1';3',1'']terphenyl-4-carboxylic acid

HRID 1158163노트

반응식

HRID 1158163 반응식
[CH2:1]([N:3]([CH2:34][CH3:35])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([O:29]CC)=[O:28])=[CH:23][CH:22]=3)[CH:13]=[CH:14][C:15]=2[O:16][CH2:17][CH2:18][CH2:19][OH:20])=[CH:6][C:5]=1[CH2:32][CH3:33])[CH3:2].[OH-].[Na+].Cl>O1CCCC1.O>[CH2:34]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([OH:29])=[O:28])=[CH:25][CH:26]=3)[CH:13]=[CH:14][C:15]=2[O:16][CH2:17][CH2:18][CH2:19][OH:20])=[CH:6][C:5]=1[CH2:32][CH3:33])[CH3:35]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11662917Ethyl 4''-diethylamino-3''-ethyl-4'-(3-hydroxypropoxy)-[1,1';3',1'']terphenyl-4-carboxylate

생성물 1

HCID 115106274''-Diethylamino-3''-ethyl-4'-(3-hydroxypropoxy)-[1,1';3',1'']terphenyl-4-carboxylic acid수율 31.4%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Into a 25 mL three-necked flask under a nitrogen atmosphere, equipped with a magnetic stirrer, are placed 270 mg (0.57 mmol) of ethyl 4″-diethylamino-3″-ethyl-4′-(3-hydroxypropoxy)-[1,1′;3′,1″]terphenyl-4-carboxylate (Example 10d) and 22 mg (5.7 mmol) of solid sodium hydroxide in 5.4 mL of tetrahydrofuran. The reaction medium is heated at the reflux temperature of the tetrahydrofuran for 5 hours. The reaction medium is concentrated under vacuum. The crude reaction product obtained is taken up in water and the pH of the medium thus obtained is adjusted to pH=4 by addition of hydrochloric acid solution in a proportion of 1 mol/L. The precipitate obtained, after stirring for 30 minutes, is purified by chromatography on silica (eluent: 40/60 heptane/ethyl acetate) to give, after evaporation of the fractions, 80 mg (yield=31%) of 4″-diethylamino-3″-ethyl-4′-(3-hydroxypropoxy)-[1,1′;3′,1″]terphenyl-4-carboxylic acid in the form of a cream-colored powder (m.p.=204° C.).

후처리

  1. customInto a 25 mL three-necked flask under a nitrogen atmosphere, equipped with a magnetic stirrer
  2. concentrationThe reaction medium is concentrated under vacuum
  3. customThe crude reaction product
  4. customobtained
  5. customthe pH of the medium thus obtained
  6. customThe precipitate obtained
  7. customis purified by chromatography on silica (eluent: 40/60 heptane/ethyl acetate)
  8. customto give

출처 및 근거

ORD 기록
ord-a1e9d2f5a86f4792be37ca5683fa5ceb
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807708B2

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