Diisopropylamine → 1-(4-Benzoylphenyl)-4,4,4-trifluoro-3-hydroxy-3-methylbut-1-yne

HRID 35886

反応式

HRID 35886 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([C:21]1[CH:26]=[CH:25][C:24]([C:27]#[CH:28])=[CH:23][CH:22]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[F:29][C:30]([F:35])([F:34])[C:31]([CH3:33])=[O:32]>O1CCCC1>[C:13]([C:21]1[CH:22]=[CH:23][C:24]([C:27]#[C:28][C:31]([OH:32])([CH3:33])[C:30]([F:35])([F:34])[F:29])=[CH:25][CH:26]=1)(=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 9871Methyl trifluoromethyl ketoneHCID 121320044-BenzoylphenylethyneHCID 178418339Butyllithium

生成物 1

HCID 199393071-(4-Benzoylphenyl)-4,4,4-trifluoro-3-hydroxy-3-methylbut-1-yne

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a cooled (-78° C.) solution of diisopropylamine (99 mL, 0.87 mmol) in freshly distilled tetrahydrofuran (5 mL) was added a solution of n-butyllithium (326 mL of a 2.5M solution in hexanes, 0.81 mmol). The solution was stirred at -78° C. for 25 minutes before a tetrahydrofuran solution of 4-benzoylphenylethyne (120 mg, 0.58 mmol) was added. The reaction was kept at -78° C. for an additional 20 minutes before 1,1,1-trifluoroacetone (521 mL, 5.8 mmol) was added in one portion. After stirring at -78° C. for 15 minutes the reaction was quenched by pouring into a saturated NH4C1 solution. The product was extracted into diethyl ether. The combined ethers were dried and evaporated. The crude product was adsorbed onto silica gel and purified by chromatography, with ethyl acetate:hexanes as the eluent (gradient 1:9 to 1:3), to yield the title compound as a white solid after trituration with hexanes (80 mg, 43%); mp 94.5°-96.0° C.; 250 MHz NMR (CDCl3): 1.76 (s,3, CH3), 2.88 (s,1, OH), 7.46-7.64 (m,5, Ar), 7.77-7.79 (m,4, Ar); MS: m/z=319(M+ 1). Analysis for C18H13F3O2 : Calculated: C, 67.92; H, 4.14; Found: C, 68.16; H, 4.15.

後処理

  1. additionwas added
  2. additionwas added in one portion
  3. customwas quenched
  4. additionby pouring into a saturated NH4C1 solution
  5. extractionThe product was extracted into diethyl ether
  6. dry with materialThe combined ethers were dried
  7. customevaporated
  8. custompurified by chromatography, with ethyl acetate

出典と根拠

ORDレコード
ord-22a7e8221edc48ff84e8e2ddd408ad1a
出典データセット
uspto-grants-1995_05
特許番号
US05411973

関連ノート

読み込み中…