Water → HCID 19801080, compound

HRID 1646652Notes

Reaction equation

HRID 1646652 reaction equation
[O:1]1[CH:3]([CH2:4][CH:5]=[C:6]([CH3:8])[CH3:7])[C:2]1([CH:10]1[CH2:15][CH:14]([OH:16])[CH2:13][CH2:12][C:11]1([CH2:18][S:19][CH3:20])[OH:17])[CH3:9].[CH3:21][N:22]([C:24]1C=CC=CN=1)C.ClCCN=[C:34]=[O:35].[OH2:36].Cl[CH2:38][Cl:39]>>[Cl:39][CH2:38][CH2:21][NH:22][C:24]([O:16][CH:14]1[CH2:13][CH2:12][C:11]([CH2:18][S:19][CH3:20])([OH:17])[CH:10]([C:2]2([CH3:9])[O:1][CH:3]2[CH2:4][CH:5]=[C:6]([CH3:8])[CH3:7])[CH:15]1[O:35][CH3:34])=[O:36]

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 160352-Chloroethyl isocyanateHCID 218852-DimethylaminopyridineHCID 19348409HCID 19348409, compound

Product 1

HCID 19801080HCID 19801080, compoundYield 69%

Procedure

To a solution of 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-1-methylthiomethyl-1,4-cyclohexanediol (1.00 g) and dimethylaminopyridine (185 ml) in dichloromethane (10 ml) was added dropwise 2-chloroethylisocyanate (0.52 ml), which was stirred overnight. To the reaction mixture was added water to suspend the reaction, then the product was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous saline solution, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, then the residue was purified by means of a silica gel column chromatography (carrier 50 g, developing solvent:ethyl acetate - hexane=1:4) to give 4-(2-chloroethylcarbamoyloxy)-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-methylthiomethylcyclohexanol (912 mg: yield 69%) as colorless powder.

Workup

  1. customthe reaction
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous saline solution
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by means of a silica gel column chromatography (carrier 50 g, developing solvent:ethyl acetate - hexane=1:4)

Sources & evidence

ORD record
ord-15258da0e5c34e3da9c32ec500f9886c
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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