Hydrochloric Acid → (3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-[4-(5-(4,4,5,5,5-pentafluoropentylsulfonyl)pentyloxy)phenyl]thiochroman

HRID 1859344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1859344
Cl.O1CCCC1.COC[O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH:15]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][S:44]([CH2:47][CH2:48][CH2:49][C:50]([F:56])([F:55])[C:51]([F:54])([F:53])[F:52])(=[O:46])=[O:45])=[CH:34][CH:33]=3)[C:16]([C:22]3[CH:27]=[CH:26][C:25]([O:28]COC)=[CH:24][CH:23]=3)([CH3:21])[CH2:17][S:18]2)=[CH:13][CH:12]=1>O>[OH:10][C:11]1[CH:20]=[C:19]2[C:14]([CH:15]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][S:44]([CH2:47][CH2:48][CH2:49][C:50]([F:55])([F:56])[C:51]([F:52])([F:53])[F:54])(=[O:46])=[O:45])=[CH:34][CH:33]=3)[C:16]([C:22]3[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=3)([CH3:21])[CH2:17][S:18]2)=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 22123606(3RS,4RS)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-4-[4-(5-(4,4,5,5,5-pentafluoropentylsulfonyl)pentyloxy)phenyl]thiochroman

Produkt 1

HCID 22123577(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-[4-(5-(4,4,5,5,5-pentafluoropentylsulfonyl)pentyloxy)phenyl]thiochromanAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Aqueous 6N--HCl solution (1 ml) was added to tetrahydrofuran solution (1.5 ml) of (3RS,4RS)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-4-[4-(5-(4,4,5,5,5-pentafluoropentylsulfonyl)pentyloxy)phenyl]thiochroman (37 mg, 0.050 mmol) and then stirred for one hour. After adding water, the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. The crude product thus obtained was purified using silica gel plate (ethyl acetate:hexane=1:2) to obtain 22 mg (yield: 70%) of the title compound.

Aufarbeitung

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe crude product thus obtained
  7. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-4fa987f31210445cb5de622f594858e0
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06153768

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