Water → HCID 22033349, compound

HRID 1792296Notes

Reaction equation

HRID 1792296 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[O:10][CH2:9][C:8]1([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[CH3:19].[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1.O>N1C=CC=CC=1.ClCCl>[CH3:18][O:17][C:13]1[CH:12]=[C:11]2[C:16]([CH:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:1][S:34]([C:31]3[CH:32]=[CH:33][C:28]([CH3:38])=[CH:29][CH:30]=3)(=[O:36])=[O:35])[C:8]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)([CH3:19])[CH2:9][O:10]2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 22033022HCID 22033022, compound

Product 1

HCID 22033349HCID 22033349, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

(3RS,4RS)-4-(5-Hydroxypentyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylchroman (430 mg, 1.2 mmol) was dissolved in a solvent mixture of pyridine (12 ml) and dichloromethane (4 ml), which was then cooled down to 0° C. p-Toluenesulfonylchloride (460 mg, 2.3 mmol) was added dropwise thereto, and the mixture was stirred at room temperature for 3 hours. Water was then added, and the organ layer was extracted with ethyl acetate. The organic extract was washed with 2N hydrochloric acid solution, dried over magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give the title compound (315 mg, yield 53%) as a colorless oil.

Workup

  1. additionwas added dropwise
  2. extractionthe organ layer was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with 2N hydrochloric acid solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-088a750a1a0243b2a737763c3b29f920
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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