Dichloromethane → HCID 58822251, compound

HRID 546476Notes

Reaction equation

HRID 546476 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].ClCCl.[Si:9]([O:26][CH2:27][CH:28]1[CH2:33][CH2:32][C@@H:31]([OH:34])[C@@H:30]([OH:35])[CH2:29]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>O>[Si:9]([O:26][CH2:27][CH:28]1[CH2:33][CH2:32][C@@H:31]([O:34][S:2]([CH3:1])(=[O:4])=[O:3])[C@@H:30]([O:35][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:29]1)([C:22]([CH3:25])([CH3:23])[CH3:24])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58822114HCID 58822114, compound

Product 1

HCID 58822251HCID 58822251, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanesulfonyl chloride (2.5 ml) was added dropwise to a dichloromethane solution (300 ml) of (1R*,2S*)-4-(tert-butyldiphenylsilyloxymethyl)-1,2-cyclohexanediol (4.2 g) and triethylamine (9.1 ml) at 0° C., and the mixture was stirred for 1.5 hours. Water was added to conduct extraction with dichloromethane, and the resultant organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by medium-pressure column chromatography on silica gel (hexane:ethyl acetate=3:2) to obtain the title compound (4.9 g) as a pale yellow oil.

Workup

  1. extractionextraction with dichloromethane
  2. washthe resultant organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by medium-pressure column chromatography on silica gel (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-6025321a5bbf4f7f8db6b3d48c0b5610
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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