Hydrochloric Acid → 3-[7-Methoxy-3-(4-methoxyphenyl)thiochroman-4-yl]benzyl alcohol

HRID 1792389Notes

Reaction equation

HRID 1792389 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]2[C:25]3[C:20](=[CH:21][C:22]([O:26][CH3:27])=[CH:23][CH:24]=3)[S:19][CH2:18][CH:17]2[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.Cl.O>O1CCCC1>[CH3:27][O:26][C:22]1[CH:21]=[C:20]2[C:25]([CH:16]([C:12]3[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=3)[CH2:9][OH:8])[CH:17]([C:28]3[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=3)[CH2:18][S:19]2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 220333824-[3-(t-Butyldimethylsilyloxymethyl)phenyl]-7-methoxy-3-(4-methoxyphenyl)thiochroman

Product 1

HCID 220332203-[7-Methoxy-3-(4-methoxyphenyl)thiochroman-4-yl]benzyl alcoholYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[3-(t-butyldimethylsilyloxymethyl)phenyl]-7-methoxy-3-(4-methoxyphenyl)thiochroman (480 mg, 0.947 mmol) was dissolved in tetrahydrofuran (40 ml), and added 3N hydrochloric acid solution (2.7 ml) thereto. The reaction mixture was stirred at room temperature for 4 h. When the reaction was completed, water was added to the reaction solution which was then extracted with ethyl acetate. The extract was washed with sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was flash chromatographied on silica gel (n-hexane:ethyl acetate=1:1) to obtain 358 mg (yield: 96%) of the title compound as a white solid.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe extract was washed with sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-306e8fbcafdb4ceabca4323d2ded0b76
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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