Diethyl Ether → 4,4,4-Trifluoro-3-hydroxy-3-fluoromethyl-1-(4-phenylsulfonylphenyl)but-1-yne

HRID 35893

反応式

HRID 35893 の反応式
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[CH:17])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[F:23][C:24]([F:30])([F:29])[C:25]([CH2:27][F:28])=[O:26].C(OCC)C>O1CCCC1>[F:23][C:24]([F:30])([F:29])[C:25]([OH:26])([CH2:27][F:28])[C:17]#[C:16][C:13]1[CH:12]=[CH:11][C:10]([S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 27605651,1,1,3-TetrafluoroacetoneHCID 199393204-PhenylsulfonylphenylethyneHCID 178418339Butyllithium

生成物 1

HCID 199393234,4,4-Trifluoro-3-hydroxy-3-fluoromethyl-1-(4-phenylsulfonylphenyl)but-1-yne

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a cooled (-78° C.) solution of 4-phenylsulfonylphenylethyne (1.68 g) in anhydrous tetrahydrofuran (70 mL) was added n-butyl lithium (3.06 mL of a 2.5 M solution in hexanes). The solution was stirred for 15 minutes at -78° C. before 1,1,1,3-tetrafluoroacetone (2.96 mL of a 40% diethyl ether solution) was added. The reaction mixture was kept at -78° C. for five minutes before quenching with 2N hydrochloric acid. Diethyl ether was added and the aqueous layer extracted further with diethyl ether. The combined organic layers were dried, evaporated and the product purified by chromatography, with diethyl ether:chloroform (1:9) as eluent. This yielded the title compound as a white solid (1.64 g) mp 119-120.8; (300 MHz) (CDCl3): 3.77 (s,1, OH), 4.55-4.79 (m,2, CH2F), 7.48-7.61 (m,5, Ar), 7.86-7.94 (m,4, Ar); MS: m/z=373 (M+1). Analysis for C17H12F4O3S: Calculated: C, 54.84; H, 3.25; Found: C, 54.70; H, 3.37.

後処理

  1. additionwas added
  2. custombefore quenching with 2N hydrochloric acid
  3. additionDiethyl ether was added
  4. extractionthe aqueous layer extracted further with diethyl ether
  5. customThe combined organic layers were dried
  6. customevaporated
  7. customthe product purified by chromatography, with diethyl ether:chloroform (1:9) as eluent

出典と根拠

ORDレコード
ord-a48ca5ea368f4fa3a151e6b6aa9489bf
出典データセット
uspto-grants-1995_05
特許番号
US05411973

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