Methyl trifluoromethyl ketone → 1-(4-Phenylsulfonylphenyl)-3-hydroxy-3-methyl-4,4,4-trifluorobut-1-yne

HRID 35885

反応式

HRID 35885 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.[Li]CCCC.[F:23][C:24]([F:29])([F:28])[C:25]([CH3:27])=[O:26]>O1CCCC1>[F:23][C:24]([F:29])([F:28])[C:25]([OH:26])([CH3:27])[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

5

反応物 3

HCID 9871Methyl trifluoromethyl ketoneHCID 199393204-PhenylsulfonylphenylethyneHCID 178418339Butyllithium

生成物 1

HCID 199393031-(4-Phenylsulfonylphenyl)-3-hydroxy-3-methyl-4,4,4-trifluorobut-1-yne収率 75.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a cooled (-78° C.) solution of 4-phenylsulfonylphenylethyne (66 mg, 0.27 mmol) in freshly distilled tetrahydrofuran (2.5 mL) was added n-BuLi (109 mL, 2.5M solution in hexanes, 0.27 mmol). The solution was stirred for 10 minutes at -78° C. at which time 1,1,1-trifluoroacetone (272 mL, 1.0M solution in tetrahydrofuran, 0.27 mmol) was added. The reaction mixture was kept at -78° C. for five minutes before quenching with 2N HCl . 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 ethyl acetate:hexanes as eluent (1:4) to yield the title butyne as a white solid (72 mg, 75%); mp 94.8°-95.3° C.; 250 MHz NMR (CDCl3): 1.72 (s,3, CH3), 3.08 (s,1, OH), 7.48-7.60 (m,5, Ar), 7.87-7.94 (m,4, Ar); MS: m/z=355(M+ 1). Analysis for C17H13F3O3S: Calculated: C, 57.62; H, 3.70; Found: C, 57.46; H, 3.65.

後処理

  1. additionwas added
  2. custombefore quenching with 2N HCl
  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 ethyl acetate

出典と根拠

ORDレコード
ord-15e03f81b99f4241a3b39f8284c311e9
出典データセット
uspto-grants-1995_05
特許番号
US05411973

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