Dimethyl Sulfide → HCID 86745884, compound

HRID 892668Notes

Reaction equation

HRID 892668 reaction equation
[CH3:1]OS(OC)(=O)=O.S(C)C.[H-].[Na+].[CH2:13]([C@@H:15]1[C:20]([CH3:22])([CH3:21])[C:19](=[O:23])[C:18]([CH3:24])=[CH:17][CH2:16]1)[CH3:14]>CS(C)=O.O.C(OCC)(=O)C.O1CCCC1>[CH2:13]([C@@H:15]1[C:20]([CH3:22])([CH3:21])[C@:19]2([O:23][CH2:1]2)[C:18]([CH3:24])=[CH:17][CH2:16]1)[CH3:14]

Participants

9

Reactant 4

HCID 1068Dimethyl SulfideHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 57085004HCID 57085004, compound

Product 1

HCID 86745884HCID 86745884, compound

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Prepared according to the method described, in a vessel equipped with a CO2 condenser and kept under N2, starting from 6.8 g (0.054 mmol) of (CH3)2SO4, 3.3 g of (CH3)2S, 6 ml of THF (tetrahydrofuran), 8 ml of DMSO and 1.7 g (0.054 mol) of 75% NaH in mineral oil. (+)-(5S)-5-Ethyl-2,6,6-trimethyl-2-cyclohexen-1-one (6.6 g, 0.033 mol, [α]20D =+82.4°) in 2 ml of DMSO was added at ~6°. The mixture was stirred over the week-end and then 21 ml of ethyl acetate were added, followed by 21 ml of water added dropwise. After the usual treatment and distillation on residues, a mixture containing 54% of the desired product was obtained. The desired epoxide was separated from the mixture by further distillation.

Workup

  1. customPrepared
  2. customdescribed, in a vessel
  3. customequipped with a CO2 condenser
  4. additionadded dropwise
  5. distillationAfter the usual treatment and distillation on residues
  6. additiona mixture containing 54% of the desired product
  7. customwas obtained
  8. customThe desired epoxide was separated from the mixture by further distillation

Sources & evidence

ORD record
ord-c38896bb4ccb4bde8aeb2d473940ba06
Source dataset
uspto-grants-1992_06
Patent number
US05118865

Reaction notes

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