Sodium Chloride → HCID 22851711, compound

HRID 55454Notes

Reaction equation

HRID 55454 reaction equation
[OH:1][C:2]1[C:3]([O:5][C@H:6]([CH3:12])[C:7]=1[C:8]([O:10][CH3:11])=[O:9])=[O:4].[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C.[Cl-].[Na+]>C1(C)C=CC=CC=1.O>[S:14]([O:1][C:2]1[C:3]([O:5][C@H:6]([CH3:12])[C:7]=1[C:8]([O:10][CH3:11])=[O:9])=[O:4])([CH3:13])(=[O:16])=[O:15]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54688321(R)-2-hydroxy-3-methoxycarbonyl-2-penten-4-olide

Product 1

HCID 22851711HCID 22851711, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

137.76 g of (R)-2-hydroxy-3-methoxycarbonyl-2-penten-4-olide are dissolved in 660 ml of toluene and at -10° C. 110 g of methanesulphonyl chloride and then, within a period of 1 hour, 97 g of triethylamine, are added. 350 ml of water and 150 ml of saturated sodium chloride solution are added, the toluene product phase is removed and the aqueous phase is re-extracted twice with 250 ml of toluene. The toluene phases are washed with sodium chloride solution and with water and concentrated by evaporation. Orange-red oil, [α]D20 =+10.6° (3% in CHCl3).

Workup

  1. customthe toluene product phase is removed
  2. extractionthe aqueous phase is re-extracted twice with 250 ml of toluene
  3. washThe toluene phases are washed with sodium chloride solution and with water
  4. concentrationconcentrated by evaporation
  5. customOrange-red oil, [α]D20 =+10.6° (3% in CHCl3)

Sources & evidence

ORD record
ord-b4d9e370a810437ea3998638c17a4655
Source dataset
uspto-grants-1997_04
Patent number
US05625059

Reaction notes

Loading…