Hydrochloric Acid → 4-(9-Hydroxynonyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

HRID 1859315Notes

Reaction equation

HRID 1859315 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]1[C:27]2[C:22](=[CH:23][C:24]([O:28][CH3:29])=[CH:25][CH:26]=2)[S:21][CH2:20][C:19]1([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[CH3:30])(C(C)(C)C)(C)C.Cl.O>O1CCCC1>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]1[C:27]2[C:22](=[CH:23][C:24]([O:28][CH3:29])=[CH:25][CH:26]=2)[S:21][CH2:20][C:19]1([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[CH3:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 220332574-[9-(t-Butyldimethylsilyloxy)nonyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

Product 1

HCID 220330054-(9-Hydroxynonyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochromanYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[9-(t-Butyldimethylsilyloxy)nonyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (400 mg, 0.72 mmol) obtained in Example 29 was dissolved in tetrahydrofuran (40 ml), and 3N--HCl (2 ml) was added thereto. The reaction mixture was stirred for 3 hours at room temperature. When the reaction is completed, water was added to the reaction solution which was then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography (n-hexane:ethyl acetate=7:3) to obtain 235 mg (yield: 74%, 3RS,4RS/3RS,4SR=9:1) of the title compound as a white solid.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with column chromatography (n-hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-f407ef5749924ef0bd8aa6b5bdf7767f
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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