Ethyl Acetate → HCID 86746495, compound

HRID 1646643Notes

Reaction equation

HRID 1646643 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([CH2:16][S:17]([CH3:19])=[O:18])([OH:15])[CH:11]([C:20]2([CH3:28])[O:27][CH:21]2[CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH:10]1[O:29][CH3:30])=[O:7])=[O:4].Cl[C:32]1[CH:37]=[CH:36]C=[C:34](C(OO)=O)[CH:33]=1.C(OCC)(=[O:44])C>ClCCl>[Cl:1][CH2:2][C:3]([NH:5][C:6]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([CH2:16][S:17]([C:19]2[CH:36]=[CH:37][CH:32]=[CH:33][CH:34]=2)(=[O:44])=[O:18])([OH:15])[CH:11]([C:20]2([CH3:28])[O:27][CH:21]2[CH2:22][CH:23]=[C:24]([CH3:25])[CH3:26])[CH:10]1[O:29][CH3:30])=[O:7])=[O:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 86746496HCID 86746496, compound

Product 1

HCID 86746495HCID 86746495, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-O-(chloroacetylcarbamoyl)-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-methylsulfinylmethyl-1,4-cyclohexanediol (300 mg) was dissolved in dichloromethane (2 ml), to which was added, under ice-cooling, m-chloroperbenzoic acid (179 mg), and the mixture was stirred for one hour. The reaction mixture was diluted with ethyl acetate (70 ml), which was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by a silica gel column chromatography (carrier 15 g, developing solvent: ethyl acetate - hexane 2:1) to afford 4-O-(chloroacetylcarbamoyl)-2-(1,2-epoxy-1,5-dimethyl-4-h-exenyl)-3-methoxy-1-phenylsulfonylmethyl-1,4-cyclohexanediol (91 mg: yield 30%) as colorless powder.

Workup

  1. additionwas added, under ice-
  2. temperaturecooling
  3. washwas washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by a silica gel column chromatography (carrier 15 g, developing solvent: ethyl acetate - hexane 2:1)

Sources & evidence

ORD record
ord-e4cc16163cff479dab3804d7cfc2ca8c
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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