Water → (3RS,4RS)-4-(8-methylsulfonyloxyoctyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochromane

HRID 1792351Notes

Reaction equation

HRID 1792351 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[S:13][CH2:12][C:11]1([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[CH3:22].C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40].O>ClCCl>[CH3:38][S:39]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[S:13][CH2:12][C:11]1([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[CH3:22])(=[O:41])=[O:40]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22033221(3RS,4RS)-4-(8-hydroxyoctyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

Product 1

HCID 22033374(3RS,4RS)-4-(8-methylsulfonyloxyoctyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochromaneYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3RS,4RS)-4-(8-hydroxyoctyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (3.25 g, 7.58 mmol) was dissolved in dichloromethane (100 ml), to which were added triethylamine (1.59 ml, 11.37 mmol) and methanesulfonyl chloride (0.88 ml, 11 37 mmol). The reaction mixture was stirred at room temperature for 1 hour. After the reaction was completed, water was added to the reaction solution, and the resulting mixture was extracted with methylene chloride. The organic layer was washed with 1M HCl solution, water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated. The product was purified by column chromatography on silica gel, eluting with 30% ethyl acetate in n-hexane to afford 3.75 g of the title compound as a pale yellow oil. (yield: 97.7%)

Workup

  1. extractionthe resulting mixture was extracted with methylene chloride
  2. washThe organic layer was washed with 1M HCl solution, water and saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe product was purified by column chromatography on silica gel
  6. washeluting with 30% ethyl acetate in n-hexane

Sources & evidence

ORD record
ord-70c2aa26b085423b84879bbc27fc4af0
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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