Dimethyl Sulfoxide → 2-Methoxy-2-(trifluoromethyl)-1,3-dioxolane

HRID 345613Notes

Reaction equation

HRID 345613 reaction equation
[F:1][C:2]([F:8])([F:7])[C:3]([O:5][CH3:6])=[O:4].Cl[CH:10]([OH:12])[CH3:11].CS(C)=O.[H-].[Na+]>O>[CH3:6][O:5][C:3]1([C:2]([F:8])([F:7])[F:1])[O:12][CH2:10][CH2:11][O:4]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 9893Methyl trifluoroacetateHCID 24758Sodium hydrideHCID 126390351-Chloroethan-1-ol

Product 1

HCID 126652842-Methoxy-2-(trifluoromethyl)-1,3-dioxolaneYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 42.0 g (0.33 mol) of methyl trifluoroacetate, 26.6 g (0.33 mol) of -chloroethanol, and 150 mL of dimethylsulfoxide (DMSO) was stirred at 10°-20° while 15.8 g (0.33 mol) of 50% NaH in mineral oil was added portionwise. The resulting mixture was stirred at 20° for 2 h, at 25° for several days, and then poured into 1 L of water. The resulting aqueous layer was extracted with 100 mL of ether. The organic layers were combined, then washed twice with water, dried over CaSO4, and distilled to give 35.6 g (63% yield) of 2-methoxy-2-trifluoromethyl-1,3-dioxolane, b.p. 60°-65° at 3.3 kPa (25 mm), and a residue containing about 4.8 g (7% yield) of by-product -(2-chloroethoxy)-2-trifluoromethyl-1,3-dioxolane (estimated by GC).

Workup

  1. additionwas added portionwise
  2. extractionThe resulting aqueous layer was extracted with 100 mL of ether
  3. washwashed twice with water
  4. dry with materialdried over CaSO4
  5. distillationdistilled

Sources & evidence

ORD record
ord-97bd41ef695f42068234e49da4c0292f
Source dataset
uspto-grants-1991_10
Patent number
US05057586

Reaction notes

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