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

HRID 1859344Notes

Reaction equation

HRID 1859344 reaction equation
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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4fa987f31210445cb5de622f594858e0
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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