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

HRID 1436640

반응식

HRID 1436640 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-5260bac620324b1db61f7ceea865017a
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618978B2

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