Diethyl Ether → HCID 88128941, compound

HRID 1646657Notes

Reaction equation

HRID 1646657 reaction equation
ClCC([NH:5][C:6]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([CH2:16][S:17][CH3:18])([OH:15])[CH:11]([C:19]2([CH3:27])[O:26][CH:20]2[CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH:10]1[O:28][CH3:29])=[O:7])=O.[CH3:30][S-:31].[CH3:32][CH2:33]OCC>CN(C)C=O>[O:26]1[CH:20]([CH2:21][CH:22]=[C:23]([CH3:24])[CH3:25])[C:19]1([CH:11]1[CH:10]([O:28][CH3:29])[CH:9]([O:8][C:6](=[O:7])[NH:5][C:30](=[S:31])[CH2:32][CH3:33])[CH2:14][CH2:13][C:12]1([CH2:16][S:17][CH3:18])[OH:15])[CH3:27]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 519392MercaptomethanideHCID 19801010HCID 19801010, compound

Product 1

HCID 88128941HCID 88128941, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide (3 ml) was dissolved 4-O-chloroacetylcarbamoyl-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-methylthiomethyl-1,4-cyclohexanediol (500 mg). To the solution was added thiomethoxide (156 mg), and the mixture was stirred for one hour. The reaction mixture was diluted with ether (50 ml), which 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. The residue was purified by means of a silica gel column chromatography (carrier 25 g, developing solvent: ethyl acetate - hexane=2:1) to give 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-4-methylthioacetylcarbamoyloxy-1-methylthiomethylcyclohexanol (407 mg: yield 79%) as colorless powder.

Workup

  1. washwas washed with a saturated aqueous solution of sodium chloride
  2. dry with materialby drying over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customThe residue was purified by means of a silica gel column chromatography (carrier 25 g, developing solvent: ethyl acetate - hexane=2:1)

Sources & evidence

ORD record
ord-7e7f3ad875484b0082e99d42ca540608
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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