Dimethyl Sulfide → HCID 53676865, compound

HRID 1456366Notes

Reaction equation

HRID 1456366 reaction equation
[O:1]=[O+][O-].[CH3:4][O:5][CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[C:17]3[CH:18]=[CH:19][C:20]([CH:22]=C)=[CH:21][C:16]=3[O:15][N:14]=2)[CH2:8]1.CSC>ClCCl>[CH3:4][O:5][CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[C:17]3[CH:18]=[CH:19][C:20]([CH:22]=[O:1])=[CH:21][C:16]=3[O:15][N:14]=2)[CH2:8]1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823Ozone2×HCID 15817481HCID 15817481, compound

Product 1

HCID 53676865HCID 53676865, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stream of ozone at -40° C. is passed for 2 hours into a solution of 8.0 g (0.029 mol) of (R)-5-(methoxymethyl)-3-(6-ethenyl-1,2-benzisoxazol-3-yl)oxazolidin-2-one in 210 ml of dichloromethane, then the ozone is driven off with a stream of argon, and 10.7 ml (0.15 mol) of dimethyl sulphide are added. The mixture is stirred for 3 hours while allowing the temperature to return to ambient temperature, and then the solvent is evaporated off under reduced pressure. By chromatography of the residue on a silica column with a mixture of 30% ethyl acetate in cyclohexane, 5.0 g of product are obtained.

Workup

  1. additionare added
  2. customto return to ambient temperature
  3. customthe solvent is evaporated off under reduced pressure
  4. additionBy chromatography of the residue on a silica column with a mixture of 30% ethyl acetate in cyclohexane, 5.0 g of product
  5. customare obtained

Sources & evidence

ORD record
ord-36b4b1423f91411aacff273e713ad5b4
Source dataset
uspto-grants-1998_12
Patent number
US05843975

Reaction notes

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