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Hydrochloric Acid → 10-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(7,7,8,8,8-pentafluoro-octyl)decanoic acid

HRID 1267758
ノート
印刷プレビュー

反応式

HRID 1267758 の反応式
[OH-].[Na+].[CH2:3]([C:5]1([C:43]2[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=2)[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([F:41])([F:40])[C:36]([F:39])([F:38])[F:37])[C:24]([O:26]CC)=[O:25])[C:13]2[C:8](=[CH:9][C:10]([OH:42])=[CH:11][CH:12]=2)[S:7][CH2:6]1)[CH3:4].Cl>O.C(O)C>[CH2:3]([C:5]1([C:43]2[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=2)[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([F:41])([F:40])[C:36]([F:38])([F:37])[F:39])[C:24]([OH:26])=[O:25])[C:13]2[C:8](=[CH:9][C:10]([OH:42])=[CH:11][CH:12]=2)[S:7][CH2:6]1)[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18546284ethyl 10-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(7,7,8,8,8-pentafluorooctyl)decanoate

生成物 1

HCID 1854627710-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(7,7,8,8,8-pentafluoro-octyl)decanoic acid収率 89.9%

試薬・触媒・溶媒 2

HCID 702
Ethanol
溶媒
HCID 962Water溶媒

実験手順

A solution of sodium hydroxide (325 mg) in water (4 ml) was added to a solution of ethyl 10-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(7,7,8,8,8-pentafluorooctyl)decanoate (558 mg, 0.81 mmol) in ethanol (8 ml). The reaction mixture was heated under reflux for 12 hours. Dilute hydrochloric acid was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=2/1) to give 10-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(7,7,8,8,8-pentafluoro-octyl)decanoic acid (480 mg, Yield 89%).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 12 hours
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent
  7. customthe residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=2/1)

出典と根拠

ORDレコード
ord-2daaf73188364408b63e2c39e3fc98fe
出典データセット
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06552068B1

反応ノート

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