Methanol → 2-(1,2-Epoxy-1,5-dimethyl-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxy-1,4-cyclohexanediol

HRID 1646653Notes

Reaction equation

HRID 1646653 reaction equation
CO.C[O-].[Na+].[SH:6][CH2:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10][OH:11].[CH3:16][C:17]([CH3:35])=[CH:18][CH2:19][C@H:20]1[O:22][C@@:21]1([C@@H:24]1[C@:29]2([O:31][CH2:30]2)[CH2:28][CH2:27][C@@H:26]([OH:32])[C@H:25]1[O:33][CH3:34])[CH3:23]>O>[O:22]1[CH:20]([CH2:19][CH:18]=[C:17]([CH3:35])[CH3:16])[C:21]1([CH:24]1[CH:25]([O:33][CH3:34])[CH:26]([OH:32])[CH2:27][CH2:28][C:29]1([CH2:30][S:6][CH2:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10][OH:11])[OH:31])[CH3:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 222778FumagillolHCID 10942334Sodium MethoxideHCID 14708630[2-(Sulfanylmethyl)phenyl]methanol

Product 1

HCID 198009842-(1,2-Epoxy-1,5-dimethyl-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxy-1,4-cyclohexanediolYield 92.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an about 14% methanol solution (6 ml) of sodium methoxide were added, under ice-cooling, 2-mercaptomethylbenzylalcohol (655 mg) and fumagillol (1.00 g). The mixture was stirred for one hour at room temperature, 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, then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by means of a silica gel column chromatography (carrier 30 g, developing solvent : ethyl acetate - hexane=2:1) to give 2-(1,2-epoxy-1,5-dimethy-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxy-1,4-cyclohexanediol (1.43 g : yield 92%) as a colorless oily substance.

Workup

  1. temperaturecooling
  2. customthe reaction
  3. extractionThe product was extracted with ethyl acetate
  4. washThe extract solution was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by means of a silica gel column chromatography (carrier 30 g, developing solvent : ethyl acetate - hexane=2:1)

Sources & evidence

ORD record
ord-7614bbc01ad345b9b90f03994e3cb942
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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