Acetic Acid → 2,2-Difluoroethenyl 4-methylbenzene-1-sulfonate

HRID 732497

반응식

HRID 732497 반응식
C([Li])CCC.[F:6][C:7](F)([F:20])[CH2:8][O:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11].C(O)(=O)C.C(OCC)(=O)C>C1COCC1>[F:20][C:7]([F:6])=[CH:8][O:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:11])=[O:12]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 178418339Butyllithium

생성물 1

HCID 109773662,2-Difluoroethenyl 4-methylbenzene-1-sulfonate수율 47.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Add n-butyllithium (1.6 M in hexanes, 4.9 mL, 7.8 mmol) dropwise over 5 min to a solution of 2,2,2-trifluoroethyl-p-toluene sulfonate (1.0 g, 3.9 mmol) in THF (20 mL) at −78° C. Stir for 30 min, add acetic acid (225 μL, 3.9 mmol) and stir for 30 min. Warm to room temperature, add ethyl acetate and extract with saturated aqueous ammonium chloride, and saturated aqueous sodium bicarbonate. Dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 0:100 to 15:85 ethyl acetate:hexanes) to give the title compound as an oil (430 mg, 47%).

후처리

  1. stirringstir for 30 min
  2. extractionextract with saturated aqueous ammonium chloride, and saturated aqueous sodium bicarbonate
  3. dry with materialDry (magnesium sulfate)
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 0:100 to 15:85 ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-1d3857bc200c4ba4b6155d3a47f970d4
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585885B2

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