Water → HCID 19801111, compound

HRID 1646654Notes

Reaction equation

HRID 1646654 reaction equation
[O:1]1[CH:3]([CH2:4][CH:5]=[C:6]([CH3:8])[CH3:7])[C:2]1([CH:10]1[CH:15]([O:16][CH3:17])[CH:14]([OH:18])[CH2:13][CH2:12][C:11]1([CH2:20][S:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][OH:30])[OH:19])[CH3:9].C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40].O>ClCCl>[O:1]1[CH:3]([CH2:4][CH:5]=[C:6]([CH3:7])[CH3:8])[C:2]1([CH:10]1[CH:15]([O:16][CH3:17])[CH:14]([OH:18])[CH2:13][CH2:12][C:11]1([CH2:20][S:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][O:30][S:39]([CH3:38])(=[O:41])=[O:40])[OH:19])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 198009842-(1,2-Epoxy-1,5-dimethyl-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxy-1,4-cyclohexanediol

Product 1

HCID 19801111HCID 19801111, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (0.5 ml) were dissolved 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxy-1,4-cyclohexanediol (100 mg) and triethylamine (64 μl). To the solution was added dropwise, under ice-cooling, methanesulfonylchloride (20 μl ). The mixture was stirred for 15 minutes, to which was added water to suspend the reaction. The product was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous solution of sodium chloride, which was then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (carrier 10 g, developing solvent: ethyl acetate - hexane=2:1) to give 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-1-(2-methanesulfonyloxymethylbenzyl)thiomethyl-3-methoxy-1,4-cyclohexanediol (98 mg: yield 83%) as a colorless oily product.

Workup

  1. additionTo the solution was added dropwise, under ice-
  2. temperaturecooling
  3. customthe reaction
  4. extractionThe product was extracted with ethyl acetate
  5. washThe extract solution was washed with a saturated aqueous solution of sodium chloride, which
  6. dry with materialwas then dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified by means of a silica gel column chromatography (carrier 10 g, developing solvent: ethyl acetate - hexane=2:1)

Sources & evidence

ORD record
ord-9f44b179086d47fc9d5ff59f06ef683a
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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