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

HRID 35886

반응식

HRID 35886 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-22a7e8221edc48ff84e8e2ddd408ad1a
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05411973

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