Triethylamine → HCID 19801120, compound

HRID 1646655Notes

Reaction equation

HRID 1646655 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]O)[OH:19])[CH3:9].C(N(CC)CC)C.[Cl-].[Li+].CS([Cl:44])(=O)=O>CN(C)C=O.O>[Cl:44][CH2:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][S:21][CH2:20][C:11]1([OH:19])[CH2:12][CH2:13][CH:14]([OH:18])[CH:15]([O:16][CH3:17])[CH:10]1[C:2]1([CH3:9])[O:1][CH:3]1[CH2:4][CH:5]=[C:6]([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 198009842-(1,2-Epoxy-1,5-dimethyl-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxy-1,4-cyclohexanediol

Product 1

HCID 19801120HCID 19801120, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide (0.5 ml) were dissolved 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxy-1,4cyclohexanediol (100 mg) and triethylamine (64 μl). To the solution was added, under ice-cooling, lithium chloride (21 mg). To the mixture was added dropwise methanesulfonyl chloride (20 μl), which was stirred for hours, then the reaction was suspended by the addition of water. The product was extracted with ether, and the extract solution was washed with a saturated aqueous solution of sodium chloride, followed by drying 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 10 g, developing solvent : ethyl acetate - hexane=1:2) to give 1-(2-chloromethylbenzyl)thiomethyl-2 -(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1,4-cyclohexanediol (70 mg: yield 67%) as a colorless oily product.

Workup

  1. additionTo the solution was added, under ice-
  2. temperaturecooling
  3. extractionThe product was extracted with ether
  4. washthe extract solution was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialby drying 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 10 g, developing solvent : ethyl acetate - hexane=1:2)

Sources & evidence

ORD record
ord-1a23bb2c46184f338fa6ca0c6111dac1
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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