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

HRID 732497

反応式

HRID 732497 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 109773662,2-Difluoroethenyl 4-methylbenzene-1-sulfonate収率 47.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-1d3857bc200c4ba4b6155d3a47f970d4
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

関連ノート

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