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

HRID 345613노트

반응식

HRID 345613 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-97bd41ef695f42068234e49da4c0292f
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05057586

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