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

HRID 1792303Notes

Reaction equation

HRID 1792303 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]

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 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(9-Hydroxynonyl)-7-methoxy-3-(4-methoxyphenyl)-3-methyl thiochroman (882 mg, 1.99 mmol) was dissolved in dichloromethane (60 ml) and triethylamine (1.38 ml, 9.96 mmol), to which was added methanesulfonylchloride (0.77 ml, 9.96 mmol). The reaction mixture was stirred at room temperature for 40 minutes. After the reaction was completed, water was added to the reaction solution, and the resulting mixture was 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 subjected to flash chromatography on silica gel (n-hexane:ethyl acetate=7:3) to give the title compound (0.74 g, yield 72%) as a colorless oil.

Workup

  1. extractionthe resulting mixture was 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

Sources & evidence

ORD record
ord-eb0b22fe5c8946d9a78a55221bd2d761
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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