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Water → 4-(9-Methanesulfonyloxynonyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

HRID 1859316
Notes
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Reaction equation

HRID 1859316 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[S:14][CH2:13][C:12]1([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[CH3:23].C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41].O>ClCCl>[CH3:39][S:40]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[S:14][CH2:13][C:12]1([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[CH3:23])(=[O:42])=[O:41]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 220330054-(9-Hydroxynonyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

Product 1

HCID 220331154-(9-Methanesulfonyloxynonyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochromanYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(9-Hydroxynonyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (131 mg, 0.30 mmol) obtained in Example 30 was dissolved in dichloromethane (12 ml) and then triethylamine (0.2 ml, 1.48 mmol) and methanesulfonyl chloride (0.11 ml, 1.48 mmol) were added thereto. The reaction mixture was stirred for 40 minutes at room temperature. When the reaction is completed, water was added to the reaction solution which was then extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The residue was purified with column chromatography (n-hexane:ethyl acetate=7:3) to obtain 141 mg (yield: 91%, 3RS,4RS/3RS,4SR=8.5/1) of the title compound as an oil.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe residue was purified with column chromatography (n-hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-eb56c4288be144d383a91581731ab27b
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06153768

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes