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Hydrochloric Acid → 10-[(3R,4R)-7-hydroxy-3-(4-hydroxyphenyl)-3-methythiochroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)decanoic acid

HRID 398074
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HRID 398074 반응식
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C@H:6]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]([CH2:34][CH2:35][CH2:36][C:37]([F:43])([F:42])[C:38]([F:41])([F:40])[F:39])[C:29]([O:31]CC)=[O:30])[C@@:7]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)([CH3:12])[CH2:8][S:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C.O>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C@H:6]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]([CH2:34][CH2:35][CH2:36][C:37]([F:43])([F:42])[C:38]([F:39])([F:40])[F:41])[C:29]([OH:31])=[O:30])[C@@:7]([C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)([CH3:12])[CH2:8][S:9]2)=[CH:4][CH:3]=1
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참가 물질

5

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HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12043771ethyl 10-[(3R,4R)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)decanoate

생성물 1

HCID 1204377210-[(3R,4R)-7-hydroxy-3-(4-hydroxyphenyl)-3-methythiochroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)decanoic acid수율 91%

시약·촉매·용매 1

HCID 19096565
Water ethanol
용매

실험 절차

Ethyl 10-[(3R,4R)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)decanoate (2.08 g, 3.297 mmol) and sodium hydroxide (527 mg, 13.19 mmol) were added to an ethanol/water mixture (40/10 ml), followed by heating under reflux for 4 hours. The reaction mixture was acidified with 2N hydrochloric acid and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane/dichloromethane=1/4/1) to give 10-[(3R,4R)-7-hydroxy-3-(4-hydroxyphenyl)-3-methythiochroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)decanoic acid (1.8 g, Yield 91%) as a foam.

후처리

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent
  6. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane/dichloromethane=1/4/1)

출처 및 근거

ORD 기록
ord-bc1627cac4364628948606b0c3140fac
출처 데이터셋
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06610733B2

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