Water → HCID 22033063, compound

HRID 1792403Notes

Reaction equation

HRID 1792403 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][CH2:22][O:23][CH3:24])=[CH:18][CH:19]=2)[O:14][CH2:13][CH:12]1[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][O:33][CH3:34])=[CH:27][CH:26]=1.C(N(CC)CC)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44].O>C(Cl)Cl>[CH3:42][S:43]([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][CH2:22][O:23][CH3:24])=[CH:18][CH:19]=2)[O:14][CH2:13][CH:12]1[C:25]1[CH:26]=[CH:27][C:28]([O:31][CH2:32][O:33][CH3:34])=[CH:29][CH:30]=1)(=[O:45])=[O:44]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22033101HCID 22033101, compound

Product 1

HCID 22033063HCID 22033063, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (3RS,4RS)-4-(9-hydroxynonyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)chroman (222 mg, 0.470 mmol) and triethylamine (0.135 ml, 0.961 mmol) in CH2Cl2 (5 ml) at 0° C. under nitrogen was added methanesulfonyl chloride (0.055 ml, 0.71 mmol). The resulting solution was stirred at 0° C. for 45 min, and then poured into H2O. The mixture was extracted with CH2Cl2. The organic layer was washed with saturated aqueous NaCl, dried over Na2SO4, filtered, and concentrated to afford (3RS,4RS)-4-(9-methanesulfonyloxynonyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)chroman (255 mg, 99%).

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. washThe organic layer was washed with saturated aqueous NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b681396a40da49328be1769d375a8d89
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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