Methanesulfonyl chloride → 1alpha,3beta-Bis(tetrahydropyran-2-yloxy)cholesta-5,7-dien-22-yl methanesulfonate

HRID 1708829Notes

Reaction equation

HRID 1708829 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]1[C@@:33]2([CH3:34])[C:12](=[CH:13][CH:14]=[C:15]3[C@@H:32]2[CH2:31][CH2:30][C@@:29]2([CH3:35])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:28])[CH:21]([OH:27])[CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11][C@@H:10]([O:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][O:38]2)[CH2:9]1.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>N1C=CC=CC=1.O>[CH3:43][S:44]([O:27][CH:21]([C@H:20]([C@@H:19]1[C@:29]2([CH3:35])[C@H:16]([C:15]3[C@H:32]([CH2:31][CH2:30]2)[C@:33]2([CH3:34])[C:12]([CH2:11][C@@H:10]([O:36][CH:37]4[CH2:42][CH2:41][CH2:40][CH2:39][O:38]4)[CH2:9][C@@H:8]2[O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[CH:13][CH:14]=3)[CH2:17][CH2:18]1)[CH3:28])[CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])(=[O:46])=[O:45]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 228438951alpha,3beta-Bis(tetrahydropyran-2-yloxy)cholesta-5,7-dien-22-ol

Product 1

HCID 867458381alpha,3beta-Bis(tetrahydropyran-2-yloxy)cholesta-5,7-dien-22-yl methanesulfonateYield 86.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

In 20 ml of pyridine was dissolved 0.58 g of the 1α,3β-bis(tetrahydropyran-2-yloxy)cholesta-5,7-dien-22-ol obtained as above. To this solution was added 0.12 g of methanesulfonyl chloride and the mixture was stirred at 0° C. for 2 hours. Then, at room temperature, the reaction mixture was diluted with water and extracted with diethyl ether. The extract was washed with water and dried over anhydrous sodium sulfate. The low-boiling fraction was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography. The procedure yielded 0.57 g of 1α,3β-bis(tetrahydropyran-2-yloxy)cholesta-5,7-dien-22-yl methanesulfonate (yield: 86%).

Workup

  1. customobtained as above
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe low-boiling fraction was then distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-916670539c234e6e8e30c1cdd1a35b08
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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